27

2. REVIEW OF LITERATURE

Carbohydrates are the most abundant class of biomolecules, making up to 75%

of the biomass on Earth.1

They are used to store energy, but also perform other

important functions in the life.2 Recently, carbohydrates and their derivatives

have emerged as an important tool for stereo selective synthesis and as a chiral

pool for the design and synthesis of the bioactive molecules. They are also used

as chiral building blocks, precursors for drug synthesis and chiral catalysts in

asymmetric catalysis.3-8

The importance of carbohydrates in biological events, the

pace of development of carbohydrate based therapeutics has been relatively slow.

This is mainly due practical synthetic and analytical difficulty. Recent advances

in the field of carbohydrate synthesis, however, have demonstrated that many of

these problems can be circumvented, and evidence the importance of

carbohydrates as bioactive substances, with regard to antibacterial, antiviral,

antineoplastic, antiprotozoal, antifungal activity. 9-15

The Preceeding text gives an overview of the therapeutic activities of

carbohydrates. These carbohydrates are generally poly or oligomeric units and

have a direct relevance with their core structure, sequence diversity, branching, N

or O linkage and overall orientations of hydrophobic and hydrophilic groups

present in the macromolecules. The highly interesting research output in cell

biology, immunology and biochemistry have help in creating general awarness

that carbohydrates contain a considerable amount of regio- and stereochemical

information which nature employs in diverse selection and directed distribution

process in multicellular organism. The role of monosaccharide derivatives for

evoking a specific biological response depends on the number of hydrophobic

and hydrophilic groups present on the molecules, number of chiral centre and on

28

the physico-chemical nature of the pharmacophore appendages to the

monosachharide. A survey of the literature indicates that only scanty information

exists about the therapeutic nature of monosaccharide in furanose form. During

initiation of present work it was, therefore, considered desirable to study the

therapeutic properties of furanose form of monosaccharide possessing appropriate

pharmacophores as appendages to the basic skeleton.

Figure 2.1: General Representation of Mannofuranoside and Glucofuranoside

Derivative

O

O O

O

O

O O

O

O

O

OO

Aglycon

Glycon: Mannofuranose Moiety

Aglycon

Glycon: Glucofuranose Moiety

2.1. D-Mannose:

D-mannose is a sugar monomer of the aldohexose series of carbohydrate.

D-mannose is a C-2 epimer of glucose. Mannose is important in human

metabolism, especially in the glycosylation of certain proteins. Several congenital

disorder of glycosylation are associated with mutation of enzymes involved in

mannose metabolism.16

2.1.1. Structure of D-Mannose:

Two of the cyclic mannose anomers possess a pyranose (six-membered)

ring, while the other two possess a furanose (five-membered) ring.

29

Figure 2.2: a; D-Mannose in Fischer projection b; α-D-mannopyranose c; β-D-

mannopyranose d; α-D-mannofuranose e; β-D-mannofuranose

O

OHOH

OH

CH2OH

O

OH

OH

CH2OH

OH

HHO

HHO

OHH

OHH

CH2OH

H

a

b c

OH

HO OH

O

H

HOHO

OH

HO OH

O

H

HOHO

d e

O

OH OH

2.1.2. Aglycon Moiety; Heterocycles:

Heterocycles form the largest group of organic chemistry and have immense

biological importance. For more than a century, heterocycles have constituted one

the largest areas of research in organic chemistry. The presence of heterocycles in

all kinds of organic compounds of interest biology and pharmacology is very well

known. Heteroatoms such as sulfur, nitrogen, oxygen and phosphorus containing

heterocyclic compounds17-19

have widespread therapeutic applications such as

antibacterial, antifungal, antimycobacterial, trypanocidal, anti-HIV activity,

30

antileishmanial agents, genotoxic, antitubercular, antimalarial, herbicidal,

analgesic, antiinflammatory, muscle relaxants anticonvulsant, anticancer and lipid

peroxidation inhibitor, hypnotics, antidepressant, antitumoral, anthelmintic and

insecticidal agents.20-25

Figure 2.3: Various Therapeutic Applications of Heterocyclic Moieties and its

Derivatives

Triazole and other heterocyclic moieties are under study since many years. Its

diversity showing the pharmacological activities is mind blowingly identified

well by the medicinal chemists.26

It shows various therapeutic activities such as

antiinflammatory27

, antimicrobials28

, β‐lactamase inhibitors29

, fungicidal30

,

insecticidal31

, antitumor32

, anticonvulsant33

, antidepressant34

, plant growth

inhibitor.35

Among various triazole and other heterocyclic derivatives, base and

Heterocycles

Antimicrobi

al activity

Antitumor

activity Antifungal

activity

Anti-

inflammatory

activity

Antiviral

activity

Anticonvulsant

activity

Antituberculor

activity

β‐lactamase

inhibitors

Plant growth

inhibitor

31

sugar modified nucleoside derivatives reflect a potent anti‐microbial activity

resulting in its application in the chemotherapy of cancer and viral infection.36

Coumarins occupy an important place in the realm of natural products and

synthetic organic chemistry.37,38

Coumarins comprise a group of natural

compounds found in a variety of plant sources in the form of benzopyrene

derivatives. Coumarins have important effects in plant biochemistry and

physiology, as they act as antioxidants, enzyme inhibitors, and precursors of toxic

substances. In addition, these compounds are involved in the form of plant

growth hormones and growth regulators, control of respiration, photosynthesis, as

well as defense against infections.39

Coumarins have long been recognized to

possess anti-inflammatory, anti-oxidant, anti-allergic, hepatoprotective, anti-

thrombotic, anti-viral and anti-carcinogenic activities.40-42

Hydroxycoumarins are

typical phenolic compounds and therefore, act as potential therapeutic agents

such as metal chelators, free radical scavengers and also extraordinary range of

biochemical and pharmacological activities of these chemicals in mammalian and

other biological systems.43,44

The coumarins are extremely variable in structure, due to the various types of

substitutions in their basic structure, which can influence their biological activity.

The interesting biological activities of the coumarins have made them attractive

targets in organic synthesis.

32

Figure 2.4: Various Therapeutic Applications of Coumarin and its Derivatives

In light of these interesting biological activities of heterocycles, it became

interested in synthesizing some new O-glycosides of substituted heterocyclic

derivatives and evaluating their antimicrobial potential.

2.1.3. O-Glycosylation of 2,3,5,6-bis-O-isopropylidene-α-D-mannofuranose

with Aglycon Moieties:

An efficient anomeric stereocontrolled glycosylation method, with high

yield of α-anomer, was reported recently by using O-glycosyl

trichloroacetamidate as a donor and alcohol as an acceptor in the presence of

catalytic amounts of TMSOTf as Lewis acid.45

Following this synthetic protocol,

2,3,5,6-di-O-isopropylidene-D-mannofuranose was prepared first by the reaction

of D-mannose with acetone in presence of catalytic amount of concentrated

sulfuric acid.46,47

This compound was selected as the glycosyl donor, was then

Coumarin &

its Derivatives

Anti-Inflammatory

Activity

Antibacterial &

Antiviral

Activity

Metal Chelators

Scavenger

Anticlotting &

Antithrombotic

Activity

Anticarcinogenic

Activity Hepatoprotective

Activity

Anti- HIV

Activity

33

coupled with alcohol acceptor of heterocyclic compounds to afford 1-O-(2-

methyl-1H-benzimidazol-1-ylmethyl)-2,3,5,6-di-O-isopropylidene-α-D-

mannofuranoside and 2-Benzothiazolylthioacetyl O-(2,3,5,6-bis-O-

isopropylidene-α-D-mannofuranosyl) L-serinemethyl ester in a good yield.

Figure 2.5: Coupling of 2,3,5,6-bis-O-isopropylidene-D-mannofuranose with

Aglycon moiety in Presence of Trimethylsilyl trifluoromethanesulfonate

(TMSOTf) and Dichloromethane48-50

O

O O

O

O

OH

+N

N

CH3

O

HN CCl3

TMSOTf

CH2Cl2

O

O O

O

O

ON

NH3C

OTMSOTf

CH2Cl2

O OO

O

O

NH

CCl3

N

S

S

O

NH

HO

O

OCH3+O

O OO

O

O

N

S

S

O

NH

O

OCH3

2.2. D-Glucose:

Glucose has 4 chiral centers. In theory, glucose may have 15 optical

stereoisomers. Only seven of them are found in living organisms. When glucose

is in its ring form, an additional asymmetric carbon, the anomeric carbon atom, is

created at C1. This leads to the formation of two ring structures (anomers), α-D-

Glucose and β-D-Glucose. In the form, the hydroxyl group attached to C-1 is

below the plane of the ring, in the β form it is above. The α and β forms

34

interconvert over a timescale of hours in aqueous solution, to a final stable ratio

of α:β 36:64, in a process called mutarotation.

2.2.1. Structure of D-Glucose:

Two of the cyclic glucose anomers possess a pyranose (six-membered)

ring, while the other two possess a furanose (five-membered) ring.

Figure 2.6`: a; D-Glucose in Fischer projection b; α-D-glucopyranose c; β-D-

glucopyranose d; α-D-glucofuranose e; β-D-glucofuranose

OH

OH

HO

O

H

HOHO

OH

OH

HO

O

H

HOHO

O

OH

OHOH

OH

CH2OH

O

OH

OH

OH

CH2OH

OH

OHH

HHO

OHH

OHH

CH2OH

OH

a

b c

d e

35

2.2.2. O-Glycosylation of 1,2,5,6-bis-O-isopropylidene-α-D-glucofuranose

with Aglycon Moieties:

Monosaccharides with good leaving groups like acylate, tosylate and

benzoate play a major role for the introduction of various functional groups, as

building blocks for the formation of di- and oligosaccharide, as chiral pool

materials or for the preparation of bioactive glycoconjugates.51-54

Alkyl and acyl

glycoses and glycoside derivatives of carbohydrates have immense importance

and some of them are biologically active.55

Protection of a particular functional

group of carbohydrates, especially monosaccharides, is not only necessary for the

modification of the remaining functional groups but also for the synthesis of

newer derivatives of great importance.56

Various methods for acylation of

carbohydrates and nucleosides have so far been developed and employed

successfully.57-59

A large number of biologically active compounds possess

aromatic and heteroaromatic nuclei. It is also known that if an active nucleus is

linked to another nucleus, the resulting nucleus may possess enhanced biological

activity.60

The benzene and substituted benzene nuclei play important role as

common denominator for various biological activities, which is also revealed by a

number of previous reports. For example, acylated n-butyl α- and β-D-

glucopyranoside were employed as test chemicals for in vitro antibacterial and

antifungal functionality test against various human pathogenic bacteria and fungi.

The study revealed that the tested n-butyl glucopyranoside derivatives showed

better antimicrobial functionalities as compared to the standard antibiotic.61

Similarly, a number of 2,3-di-O-acyl derivatives of methyl 4-O-acetyl-α-L-

rhamnopyranoside were screened against bacterial and fungal pathogens. The

study revealed that the acylated rhamnopyranoside derivatives are more prone

towards antifungal activities than that of antibacterial activities.62

Synthesis of

36

some acylated monosaccharide derivatives (e.g. D-glucose) in furanose and

pyranose form containing various acyl and aromatic moieties in a single

molecular framework and evaluated their comparative antimicrobial activities

using a variety of bacterial and fungal pathogens.

Figure 2.7: Methyl 4,6-O-benzylidene-α-D-glucopyranoside, Methyl 4,6-O-

benzylidene-α-D-mannopyranoside and a Number of its Derivatives were

Screened for in vitro Antibacterial and Antifugal Activity Against Various

Bacterial and Fungal Strains 63-66

O

R1O

OMe

OR

O

O

Ph

O

RO

OMe

O

O

Ph

OR1

a b

R = R1 = H R = R1 = H

R = Stearoyl, R1 = H R = 4-Cl, Bz; R1 = Ac

R = Stearoyl, R1 = Ac R = 4-Cl, Bz; R1 = Bz

R = Stearoyl, R1 = Bz R = 4-Cl, Bz; R1 = Octanoyl

R = Stearoyl, R1 = pTs R = 4-Cl, Bz; R1 = Decanoyl

Mono-substituted mannofuranose and glucofuranose derivatives were

investigated for their antimicrobial activity against a range of pathogenic bacteria

and fungi.

37

Figure 2.8: Some Acylated Derivatives of benzyl 2,3-O-isopropylidene-α-D-

mannofuranoside and 1,2,5,6-d-O-isopropylidene-α-D-glucofuranose Investigated

for in vitro Antimicrobial Activity Against Various Strains67,68

O

O

O

O

OOR

O

O O

R2O

R1O

OBn

cd

R1 = H; R2 = H R = H

R1 = Myr; R2 = H R = Ms

R1 = Myr; R2 = Ac R = Laur

R1 = Myr; R2 = Bz

Carbohydrate fatty acid ether and esters are another class of fatty acid derivatives

shown a significant activity, and they have broad applications in the food

industry.69-71

They are most commonly employed as surfactants, their

antimicrobial properties have been reported. The use of carbohydrate esters is

continually increasing as they are completely biodegradable, they are not harmful

to the environment and they are non-toxic.72

Another attractive feature of

carbohydrate fatty acid derivatives is the potential to modify their properties by

controlling the degree of substitution of the carbohydrate, by varying the nature

of the fatty acid and also the sugar itself. They are currently being employed in

38

the food, cosmetic and detergent industry.73

Sugar esters are widely used in Japan

as antibacterial agents in canned drinks.

Figure 2.9: Synthesis of Ether and Ester Carbohydrate Derivatives74,75

O

O

O

O

OOH

DMF anhydrous

1-chlorododecaneNaH, 0°C-RT

O

O

O

O

OO

C11H23

O

O

O

O

OOH

Py. anhydrous

DMAP, LauroylChloride, RT

O

O

O

O

OO

C11H23

O

The primary screening of synthesized compounds was done by well diffusion

method. Antimicrobial efficacy of the synthesized compounds was compared

with commercially available compounds such as Ampicillin and fluconazole

which have proven antimicrobial activity. Compounds efficacy was compared

using an absorbance based broth micro dilution assay to determine the Inhibitory

Concentration (IC50).76-85

39

2.3. References:

1. Ferreira, VF, da Rocha DR. Silva FCda, (2009), ‘Potentiality and

Opportunity in Chemistry of Sucrose and Other Sugars’, Quim. Nova,

32(3): 623-638.

2. Stick RV., (2001), ‘Carbohydrates: The Sweet Molecules of Life’,

Academic Press, p. 256.

3. Diéguez M, Pàmies O, Ruiz A, Díaz Y, Castillón S, Claver C., (2004),

‘Carbohydrate derivative ligands in asymmetric catalysis’, Coord. Chem.

Rev., 248: 2165-2192.

4. Diéguez M, Pàmies O, Claver C., (2004), ‘Ligands Derived from

Carbohydrates for Asymmetric Catalysis’, Chem. Rev., 104: 3189-3215.

5. Woodward S, Diéguez M, Pàmies O., (2010), ‘Use of sugar-based ligands in

selective catalysis. Recent developments’, Coordination Chemistry

Reviews, 254: 2007-2030.

6. Diéguez M, Claver C, Pàmies O., (2007), ‘Recent progress in asymmetric

catalysis using chiral carbohydrate-based ligands’, Eur. J. Org. Chem.,

4621-4634.

7. Boysen MMK., (2007), ‘carbohydrates as synthetic tools in organic

chemistry’ Chem. Eur. J., 13(31): 8648-8659.

8. Appelt HR, Limberger JB, Weber M, Rodrigues OED, Oliveira JS, Lüdtke

DS, Braga AL., (2008), ‘Carbohydrates in asymmetric synthesis:

enantioselective allylation of aldehydes’, Tetrahedron Letters, 49: 4956-

4957.

9. Nogueira CM, Parmanhan BR, Farias PP, Corrêa AG., (2009), ‘The growing

importance of carbohydrates in medicinal chemistry’, Rev. Virtual Quim.

1(2):149-159.

40

10. Chi-Huey Wong (Ed.) ‘Carbohydrate-based Drug Discovery, Wiley-VCH

Verlag GmbH & Co. KGaA: Weinheim, 2003.

11. Shen Yi , Sun Yufeng , Sang Zhipei , Sun Chengjun , Dai Ya , and Deng

Yong, (2012), ‘Synthesis, Characterization, Antibacterial and Antifungal

Evaluation of Novel Monosaccharide Esters’, Molecules, 17:8661-8673;

doi:10.3390/molecules1707866

12. Aboelmagd A., Ali Ibrahim A. I., Salem Ezzeldin M. S. and Abdel-Razik

M., (2011), ‘Synthesis and antifungal activity of some 2-

benzothiazolylthioacetyl amino acid and peptide derivatives, ARKIVOC

(ix):337-353.

13. Synthesis and antimicrobial activities of 3-O-Methyl-(R)-1,2-O-

trichloroethylidene-α-D-xylo-furanuronic acid and 3-O-Methyl-(S)-1,2-O-

trichloroethylidene-α-D-xylo-furanuronic acid, (2013), 13rd International

conference on Synthetic Organic Chemistry (ECSOC-13), 1-30.

14. Sofan Mamdouh A., Said Samy B., Kandeel Said H., (2012) ‘Antimicrobial

Activity of Newly Synthesized Thiadiazoles, 5-benzyl-2Htetrazole and

Their Nucleosides, Der Pharma Chemica 4 (3):1064-1073.

15. Matin Mohammed M., Bhuiyan M.M.H., Debnath Dulal C., Manchur M.A.,

‘Synthesis and comparative antimicrobial studies of some acylated D

glucofuranose and D-glucopyranose derivatives’, Int. J. Biosci. 3(8)

:279-287.

16. Freeze HH, Sharma V., (2010). ‘Metabolic manipulation of glycosylation

disorders in humans and animal models’. Seminars in Cell &

Developmental Biology, 21 (6): 655–662.

17. Valverde MG, Torroba T., (2005), ‘Sulfur-Nitrogen Heterocycles’

Molecules, 10: 318-320.

41

18. Liu RS., (2001), ‘Synthesis of oxygen heterocycles via alkynyltungsten

compounds’, Pure Appl. Chem., 73(2): 265-269.

19. Reddy GPV, Kiran YB, Reddy SC, Reddy D.C., (2004), ‘Synthesis and

antimicrobial activity of novel phosphorus heterocycles with exocyclic p-

C link’, Chem. Pharm. Bull., 52(3): 307-310.

20. Mittal A., (2009), ‘Synthetic Nitroimidazoles: Biological Activities and

Mutagenicity Relationships’, Sci. Pharm., 77: 497-520.

21. Nagalakshmi G., (2008), ‘Synthesis, Antimicrobial and Antiinflammatory

Activity of 2,5 Disubstituted-1,3,4-oxadiazoles’, Indian J. Pharm. Sci.,

70(1): 49-55.

22. Joule JA, Mills K., (2000), ‘Heterocyclic Chemistry’, 4th ed., Blackwell

Science, Oxford 2000, p. 589.

23. Nekrasov DD., (2001) ‘Biological Activity of 5- and 6-Membered

Azaheterocycles and Their Synthesis from 5-aryl-2,3-dihydrofuran-2,3-

diones’, Chemistry of Heterocyclic Compounds, 37(3): 263-275.

24. Sperry JB, Wright DL., (2005), ‘Furans, thiophenes and related

heterocycles in drug discovery’, Current Opinion in Drug Discovery and

Development, 8(6): 723-740.

25. Polshettiwar V, Varma RS., (2008), ‘Greener and expeditious synthesis of

bioactive heterocycles using microwave irradiation’, Pure Appl. Chem.,

80 (4): 777-790.

26. Katica CR, Vesna D, Vlado K, Dora GM, Aleksandra B., (2001), ‘Synthesis,

antibacterial and antifungal activity of 4‐substituted ‐5‐aryl

‐1,2,4‐triazole’ Molecules, 6: 815‐824.

27. Singh RJ., (2009), ‘1,2,3‐Triazole derivatives as possible antiinflammatory

agents’, Rasayan J. Chem. 2(3): 706‐708.

42

28. Griffin DA, Mannion SK., (1986), ‘Preparation of substituted

triazolylbutanoates as plant growth regulators’, Eur. Pat. Appl. 199: 474.

Chem. Abstr. 1987 106, 98120u.

29. Timo Weide, Adrian Saldanha S, Dmitriy Minond, Timothy P, Spicer, Joseph

R, Fotsing, Michael Spaargaren, Jean‐Marie Frere, Carine Bebrone, Barry K,

Sharpless, Peter S, Hodder, Valery V, Fokin NH., (2010), ‘1,2,3‐Triazole

inhibitors of the VIM‐2 metallo‐β‐lactamase’, ACS Med. Chem. Lett.,

1(4): 150–154.

30. Heubach G, Sachse B, Buerstell H., (1979), ‘1,2,4‐Triazole derivatives’,

Ger. Offen, 2: 826,760.(Chem. Abstr. 1980, 92, 181200h).

31. Tanaka G., (1974), ‘Triazole derivatives’, Japan Kokai, 973:7495.

32. Jenkins TC, Stratford IJ, Stephens MA., (1989), ‘3‐Nitro‐1,2,4‐triazoles as

hypoxia‐selective agents’, Anticancer Drug Des., 4 : 145–160.

33. Husain MI, Amir M., (1986), ‘Synthesis of some new substituted

thiosemicarbazides and triazoles as possible anticonvulsants’, J. Indian

Chem. Soc., 63: 317–319.

34. Chiu SHL, Huskey SEW., (1998), ‘Species differences in N-

glucuronidation’, Drug Metabol. Dispos., 26: 838–847.

35. Eliott R, Sunley RL, Griffin DA., (1986), ‘Preparation of plant growth

regulant triazoles and imidazoles’, UK Pat Appl GB., 2: 175-301.

36. Singh G, Sharma P, Dadhwal S, Garg P, Sharma S, Mahajan N, Rawal S.,

(2011), ‘Traizoles- Impinging the bioactivities’, Int J. Cur.r Pharm. Res.,

3(2): 105-118.

37. Murray RDH., (1991), ‘Naturally occurring plant coumarins’, Prog.

Chem. Org. Nat. Prod., 58: 83-316.

43

38. Selim, M., (1992), ‘ Reactions of 3-Carboethoxy-6-bromo coumarins’

Chemical Abstracts (vol. 117, no. 27 ), page no. 811, XP002053889

39. Murray RDH, Mendez J, Brown SA., The Natural Coumarins: Occurance,

Chemistry and Biochemistry, John Wiley & Sons, New York, 1982.

40. Jung, K, Park YJ, Ryu, JS., (2008), ‘Scandium (III) triflate catalysed

coumarine synthesis’, Synth. Commun., 38(24): 4395-4406.

41. O'Kennedy R, Thornes RD., Coumarins: Biology, Applications and Mode

of Action, John Wiley & Sons, Chichester, 1997.

42. Zahradnik M. The Production and Application of Fluorescent Brightening

Agents, John Wiley & Sons, 1992.

43. Paya, M, Halliwell B, Houl JRS., (1992), ‘Interaction of series of

coumarins with reactive oxygen species’ Biochem. Pharmacol., 2(44): 205-

214.

44. Sharma DK., (2006), ‘Phramacological properties of flavonoids including

flavonoligans-integration of petrocrops with drug development from

plants’ Journal of Scientific and Industrial Research, 65: 477-484.

45. Ali, IAI, Ashry El, Schmidt ESH, (2003), ‘Protection of hydroxyl groups

with diphenylmethyl and 9-fluorenyl trichloroacetimidates -effect on

anomeric stereocontrol’, Eur. J. Org. Chem., 4121-4131.

46. de Belder AN., (1965), ‘Cyclic acetals of the aldoses and aldosides’, Adv

Carbohydr Chem biochem, 20: 219-302.

47. de Belder AN., (1977), ‘Cyclic acetals of the aldoses and aldosides:

Highlights of the literature since 1964 and a supplement to the tables’,

Adv. Carbohydr. Chem. Biochem., 34: 179-241.

48. Ahmed OH, Nezhawy El, Samir T, Gaballah, Mohamed AA, Radwan,

Ayman R, Baiuomy, Omar ME, Abdel-Salam, (2009), ‘Structure-Based

44

Design of Benzimidazole Sugar Conjugates: Synthesis, SAR and In Vivo

Anti-inflammatory and Analgesic Activities’, Medicinal Chemistry, 5:

558-569.

49. Aboelmagd A, Ibrahim AI, Ali, Ezzeldin MS, Salem, Abdel-Razik M.,

(2011), ‘Synthesis and antifungal activity of some 2-

benzothiazolylthioacetyl amino acid and peptide derivatives’, ARKIVOC,

(ix): 337-353.

50. Bassyouni FA, Abdel All AS, Haggag WM, Mahmoud M, Sarhan MM,

Abdel-Rehim M. (2012), ‘Synthesis of triazole, pyrazole, oxadiazine,

oxadiazole, and sugar hydrazone-5-nitroindolin-2-one derivatives ( part

I)’, Egypt Pharmaceut J, 11:129-35.

51. Lindhorst TK., Essentials of Carbohydrate Chemistry and Biochemistry,

2nd ed. Wiley-VCH, Weinheim, Germany, 2003.

52. Andary C, Wylde R, Laffite C, Privat G, Winternitz I., (1982), ‘Structures of

verbascoside and orobancoside caffeic acid sugar esters from Orobanche

rapumgenistae’, Phytochem., 21: 1123–1127.

53. Kabir AKMS, Matin MM, Kabir MF, Anwar MN., (1998), ‘Antibacterial

activities of some selectively acylated monosaccharide derivatives’,

Chittagong Univ. J. Sci., 22:117–124.

54. . Kabir AKMS, Matin MM, Sanaullah AFM, Sattar MA, Rahman MS.,

(2001), ‘Antimicrobial activities of some lyxosidederivatives’, Bangladesh

J. Microb., 18: 89–95.

55. Guthrie RD, Honeyman J., An Introduction to the Chemistry of

Carbohydrates, 3rd ed. Oxford, UK., 1968.

45

56. Moyer BG, Pfeffer PE, Moniot JL, Shamma M, Gustine DL., (1977),

‘Corollin, coronillin and coronarian: Three new 3-nitropropanoyl-D-

glucopyranoses from Coronilla varia’, Phytochemistry, 16: 375-377.

57. Tsuda Y, Haque ME., (1983), ‘Regioselective introduction of p-coumaroyl

group to α-L-arabino-pyranosides. Total synthesis of Inundoside-G and

Inundoside-D1’, Chemical and Pharmaceutical Bulletin (Japan), 31:1437-

1439.

58. Andry C, Wylde R, Laffite C, Privat G, Winternitz I., (1982), ‘Structures of

verbascoside and orobanchoside, caffeic acid sugar esters from

Orobanche rapumgenistae’, Phytochemistry, 21: 1123-1127.

59. Kabir AKMS, Matin MM, Ali M, Anwar MN., (2003), ‘Comparative

studies on selective acylation and antimicrobial activities of some D-

glucofuranose derivatives’, Journal of Bangladesh Academy of Science,

27: 43-50.

60. Gupta R, Paul S, Gupta AK, Kachroo PL, Bani S., (1997), ‘Synthesis and

biological activities of some 2-substituted phenyl-3-(3-alkyl/aryl-5,6-

dihydro-s-triazolo[3,4-b][1,3,4]thiazolo-6-yl)-indoles’, Indian Journal of

Chemistry, 36 (B): 707-710.

61. Matin MM, Bhuiyan MMH, Azad AKMS., (2013), ‘Synthesis and

antimicrobial evaluation of some n-butyl α and β-D-glucopyranoside

derivatives’, RGUHS Journal of Pharmaceutical Science (India), 3: 53-59.

62. Matin MM, Ibrahim M, Rahman MS., (2008), ‘Antimicrobial evaluation of

methyl 4-O-acetyl-α-L-rhamnopyranoside derivatives’, Chittagong

University Journal of Biological Science, 3: 33-43.

46

63. Abdul KMS, Kabir, Pijus D, Anwar MN., (2005), ‘Antimicrobial Screening

of Some Acylated Derivatives of D-Glucose’, Int. J. of Agr. & Biology, 5:

757–759.

64. Abdul KMS, Kabir, Pijus D, Anwar MN., (2005), ‘Antibacterial and

Antifungal Evaluation of Some Derivatives of Methyl α-D-

Mannopyranoside’, Int. J. of Agr. & Biology, 5: 754–756.

65. KAWSAR SARKAR M. A., KABIR ABUL K. M. S., BHUIYANAND

MOHAMMAD M., MANIK MOHAMMAD M. R., (2012), ‘SYNTHESIS

AND CHARACTERIZATION OF METHYL 4, 6-O-ENZYLIDENE-α-

D-GLUCOPYRANOSIDE DERIVATIVES’, Journal of Bangladesh

Chemical Society, Vol. 25(2):101-109.

66. KAWSAR SARKAR M. A., KABIR ABUL K. M. S., BHUIYAN

MOHAMMAD M. R., FERDOUS JANNATUL AND RAHMAN

MOHAMMAD S., (2013) ‘SYNTHESIS, CHARACTERIZATION AND

MICROBIAL SCREENING OF SOME NEW METHYL 4, 6-O-(4-

METHOXYBENZYLIDENE)-α-DGLUCOPYRANOSIDE

DERIVATIVES’, Journal of Bangladesh Academy of Sciences, Vol. 37(2):

145-158.

67. Abdul KMS, Kabir, Mohammed M, Matin, Mohammad MR, Bhuiyan,

Mohammed A, Rahim, Safiqur-Rahmab MD., (2005), ‘Biological

Evaluation of Some Monosaccharide Derivatives’, Int. J. of Agr. &

Biology, 2: 218–221.

68. Mohammed M, Matin MMH, Bhuiyan, Dulal C, Debnath MA, Manchur,

(2013), ‘Synthesis and comparative antimicrobial studies of some

acylated D-glucofuranose and D-glucopyranose derivatives’,

International Journal of Biosciences, 3 (8): 279-287.

47

69. Ved H S, Gustow E, Mahadevan V, Pieringer RA., (1984),

‘Dodecylglycerol, A new type of antibacterial agent which stimulates

autolysin activity in Streptococcus faecium ATCC 9790’, J. Biol. Chem.,

259 (13): 8115-8121.

70. Nakamura S., (1997), ‘Oleochemicals: Sucrose fatty acid esters used as

food emulsifiers are more widely used in Japan than anywhere else’,

American oil chemists society, Inform-campaign, 8 (8): 866-872.

71. Watanabe, T., (1999), ‘Sucrose fatty acid esters, Past, present and future’,

Foods Food Ingr. J. Jpn., 180: 18-25.

72. Marshall DL, Bullerman LB., (1994), ‘Antimicrobial properties of sucrose

fatty acid esters. In Carbohydrate Polyesters as Fat Substitutes’, (ed. C.C.

Akoh and B.G. Swanson) pp. 149-167, Marcel Dekker, Inc., N.Y.

73. Ganske F, Bornscheuer UT., (2005), ‘Lipase catalyzed glucose fatty acid

ester synthesis in ionic liquids’, Org. Lett., 7: 3097-3098.

74. Samal PK, Maier ME., (2003), ‘Acetal-vinyl sulphide cyclisation on sugar

substrate: Effect of structure and substituents’, J. Org. Chem., 68: 824-

831.

75. Chevalier R, Colsch B, Afonso C, Baumann N, Tabet JC, Mallet JM., (2006),

‘Synthetic sulfated glucuronosyl paragloboside (SGPG) and its uses for

the detection of autoimmune peripheral neuropathies’, Tetrahedron,

62(4): 563-577.

76. Ayşe N, Duygu ATI, Hakkı A, Tansel OY, İsmet DG, İsmail K., (2008),

‘Antimicrobial and Cytotoxic Activities of Zingiber officinalis Extracts’,

FABAD J. Pharm. Sci., 33: 77–86.

48

77. Dulger G, Aki C., (2009), ‘Antimicrobial Activity of the Leaves of

Endemic Stachys pseudopinardii in Turkey’, Tropical Journal of

Pharmaceutical Research’, 8 (4): 371-375

78. Annette W, Fothergill, Michael G, Rinaldi, Deanna A, Sutton, (2006),

‘Antifungal Susceptibility Testing’, Infect Dis. Clin N Am., 20: 699–709.

79. Christina Kratzer, Selma Tobudic, Monika Schmoll, Wolfgang Graninger,

Apostolos Georgopoulos, (2006), ‘In vitro activity and synergism of

amphotericin B, azoles and cationic antimicrobials against the emerging

pathogen Trichoderma spp.’, Journal of Antimicrobial Chemotherapy, 58:

1058–1061.

80. Baur AW, Kirby WMM, Sherris JC, Turch M., (1966), ‘Antibiotic

susceptibility testing by a standardized single disk method’, Am.J. Clin.

Pathol., 45: 493-496.

81. Amsterdam D., Susceptibility testing of antimicrobials in liquid media, In

Lorian V. editor, Antibiotics in Laboratory Medicine, Baltimore, Williams

&Wilkins, pp. 72–78, 1991.

82. Scott Pryor W, Donna Gibson M, Gary Bergstrom C, Larry Walker P.,

(2007), ‘Minimization of between-well sample variance of antifungal

activity using a high-throughput screening microplate bioassay’,

BioTechniques, 42: 168-172.

83. Hadacek F, Greger H., (2000), ‘Testing of antifungal natural products,

methodologies, comparability of results and assay choice’, Phytochem.

Anal., 11: 137-147.

84. Grover R.K, Moore JD., (1962), ‘Toximetric studies of fungicides against

the brown rot organisms Sclerotiana flucticola and S. laxa’, Phytopathol.,

52: 876–880.

49

85. Miah MAT, Ahmed HU, Sharma NR, Ali A, Miah SA., (1990), ‘Antifungal

activity of some plant extracts’, Bangladesh. J. Bot., 19: 5–10.