Evaluation of Benzimidazole Derivatives by using Aldehydes

 

Arvind Kumar Singh, Ekta Khare, Hridesh Singh Chauhan

 

ABSTRACT:

A novel series of Benzimidazole derivatives were synthesized and characterized by using different types of aldehydes. Benzimidazole is heterocyclic fused aromatic organic compound which consists of benzene and imidazole.In the present work, a set of 2- substituted Benzimidazole were successfully synthesized by condensation of o-phenylene diamine with p- amino benzoic acid in presence of 4N HCl. These compounds were screened for antibacterial and antifungal activity. Final compounds were purified and their chemical structures have been confirmed by I.R., 13 C N.M.R., 1 H N.M.R., MASS Spectra.

 

 

INTRODUCTION:

All the heterocyclic compounds have a great interest in pharmaceutical chemistry. Out of these heterocyclic compounds the benz fused heterocyclic compounds i.e. benzimidazole and its derivatives have wide variety of biological activities in which benzimidazole have played a very important role in development of theory in heterocyclic chemistry. Benzimidazole drugs are widely used for prevention and treatment of various infection.¹ Benzimidazole and its derivatives is an important class of bioactive molecules in field of Drug and Pharmaceuticals². Benzimidazole is fused aromatic imidazole ring system where benzene ring is fused to the 4 and 5 position of an imidazole ring.This benzimidazole is also known as 1,3-benzodiazoles³. These compounds have different activities as they can act as bacteriocides, bacteriostat  as well as fungicides. Benzimidazole are remarkably effective compound, extensive biochemical and pharmacological studies have confirmed that these molecules are effective against various stains of  microorganisms⁴.

 

Antibacterial activity-

1-Reported the synthesis of 2-{2-(5-phenyl-1H-tetrazol-1yl) phenyl}-1-H-benzimidazole, having antimicrobial activity against gram positive Staphylococcus aureus and gram negative Escherichia coli bacteria^5.

 

2-Reported the synthesis of 2-substituted benzimidazole which shows antimicrobial activity.⁶

 

 

3- Reported the synthesis of selenadiazolo Benzimidazole which shows the antimicrobial activity against gram positive and gram negative bacteria.⁷

 

 

4- Reported the synthesis of 4-(1H benzimidazole-yl(1hydroxy benzal) amino) benzoic acid which shows the antimicrobial activity.⁸

 

5- Reported the synthesis of Pyridyl-oxy-Cycloexane Carboxylic Acid Benzimidazole derivative having antimicrobial activity against DGAT 1 inhibitor.⁹

 

 

6- Reported the synthesis of 5-amino-2-substituted Benzimidazole which shows the antimicrobial activity.¹⁰

 

 

7- Reported the synthesis of 2-aryl-1-aryl-methyl-1-H-1,3-benzimidazole derivatives which shows the antimicrobial activity.¹¹

 

 

8- Reported the synthesis of 2-chloro methyl benzimidazole derivative which shows the antimicrobial activity.¹²

 

 

9- Reported the synthesis of 2, 3-dihydro 2-[(2-acytyl oxyl)phenyl]-1H-benzo imidazole which shows the antimicrobial activity.¹³

 

10- Reported the synthesis of [(1-H-benzo imidazol-2-yl)phenyl]-3-chloro 4-(4-substituted phenyl)azetidin-2-one which shows the antimicrobial activity.¹⁴

 

11- Reported the synthesis of 3-benzoyl benzimidazole derivatives which shows antimicrobial activity against A. fumigates.¹⁵

 

 

 

12- Reported the synthesis of 7-(1-H-benzimidazole-2-yl)-5-substituted phenyl pyrido pyrimidin-4-amine which shows the antimicrobial activity.¹⁶

 

13- Reported the synthesis of 2N-[2-(1H benzo imidazol-2-yl) phenyl]-N-phenyl benzamide which shows the antimicrobial activity.¹⁷

 

R=COCH₃, H, C₆H₅

 

14- Reported the synthesis of mannich base of benzimidazole derivatives, having antimicrobial activity.¹⁸

 

15- Reported the synthesis of N-substituted 2-substituted- benzimidazole derivatives having antimicrobial activity.¹⁹

 

 

16- Reported the synthesis of carbonyl-amide linkage based Benzimidazole derivatives which shows antibacterial activity.²⁰

 

17- Reported synthesis of 4-(1H-benzo imidazol-2yl) benzenamine., having antimicrobial activity.²¹

Where R=

 

18- Reported the synthesis of N-alkyl and N-acyl derivative of 2-(4-thiazolyl)1-H-Benzimidazole which shows antimicrobial activity.²²

 

R=Cl,Br,NH₂

 

19- Reported the synthesis of phenyl substituted benzyl ether benzimidazole derivatives which is evaluated for antibacterial activity against S.aureus and E.coli bacteria.²³

 

R=CH₃, C₂H₅

 

20- Reported the synthesis of (4-chloro pyridine-2-yl)[2-(dimethyl amino)methyl] 1-H-benzo imidazol-1yl methanones which shows antimicrobial activity.²⁴

 

21- Reported the synthesis of dimethyl (substituted-1, 3-benzathiazol-2 yl)dithio imidocarbonate derivatives which shows the antimicrobial activity.²⁵

 

 

 

 

22- Reported the synthesis of 3-benzoyl benzimidazole derivatives was evaluated against gram positive and gram negative bacteria.²⁶

 

 

23- Reported the synthesis of 2-amino methyl benzimidazole derivatives which shows the antimicrobial activity.²⁷

 

 

24- Reported the synthesis of novel benzimidazole derivatives which shows the antimicrobial activity.²⁸

 

25-Reported the synthesis of 3-(2-methyl benzimidazole-1-yl)-N-(2-aryl 2-oxo[1,3]thiazolidin-3-yl)Propionamide having potent antimicrobial activity.²⁹

 

 

26- Reported the synthesis of 1-(substituted methyl)-2-(substituted phenyl) benzimidazole which shows antimicrobial activity.³⁰

 

R= CH₃, C₂H₅

 

 

27- Reported the synthesis of 2-substituted benzimidazole-1-carbodithioate derivatives which shows antimicrobial activity.³¹

 

 

28- Reported the synthesis of 2-(2 substituted -1H-benzimidazol-1-yl) acetohydrazide, having antimicrobial activity.³²

 

 

29- Reported the synthesis of alkyl thioaryl substituted benzimidazole derivatives which shows antimicrobial activity.³³

 

30- Reported the synthesis of S-alkylated and aryl alkylated derivatives of C-substituted benzimidazole derivatives like 4,6 didichloro-2-(dimethyl amino eth-1-yl) benzimidazole hydrochloride and other is 5,6-dichloro-2-(dimethyl amino prop-1-yl-thio) benzimidazole hydrochloride which shows the antimicrobial activity.³⁴

S alkylated derivatives of C-substituted benzim idazole

 

R=CH₂CH₂N(CH₃)₂

R₁=H, R₂=R₃=CH₃

 

Antifungal activity-

31- Reported the synthesis of 5-substituted derivatives of benzimidazole  which shows antifungal activity.³⁵

 

R=CH₃, I₂

 

32- Reported one pot synthesis of benzimidazole using lanthanum chloride which shows antifungal activity.³⁶

 

R=H, Alkyl, Aryl

 

 

33- Reported the synthesis of 5-((2-methyl 1H-benzimidazole-1yl)methyl)-1,3,4-oxadiazole-2-thione which shows antifungal activity.³⁷

 

34- Reported the synthesis of novel 2-(2-benzisoxazol-3-yl) ethyl)-1H-benzimidazol which shows antifungal activity.³⁸

 

R=CH₃, OH, Br

35- Reported the synthesis of new substituted fluoro benzimidazole derivatives having antifungal activity.³⁹

 

 

R=Cl, R=-OC₆H₅

 

36- Reported the synthesis of D.N.A. cleavage of Benzimidazole derivatives which shows antifungal activity.⁴⁰

 

 

 

37- Reported the synthesis of  2-chloro methyl-1-H-benzimidazole derivatives which shows antifungal activity.⁴¹

 

38- Reported the synthesis of novel Benzimidazole derivatives of fungicidal activity against fungal species like A.flavus, A.fumigatus, C.albidus.⁴²

 

R=CH₃,OH, NO₂

 

39-Reported the synthesis of 2-methyl benzimidazole derivative 4-[1-(4-substituted phenyl)-2-hydroxy-3-(2-methyl-benzimidazole-1yl)-3-oxo-propyl-amine] substituted aromatic amino derivatives of fungicidal activity against fungal species.⁴³

 

 

40- Reported the synthesis of novel benzimidazole derivatives which shows antifungal activity like 1-nonyl-1-H-benzoimidazole and 1 decyl-1 Hbenzo[d] imidazole.⁴⁴

 

41-) Reported the synthesis of some novel benzimidazole derivatives by substituting triazole moiety having fungicidal activity.⁴⁵

 

X=Cl, NO₂,OH, NH₂

 

 

42- Reported the synthesis of novel benzimidazole derivatives as 1-methyl-2-substituted phenoyl methyl benzimidazole derivatives which shows antifungal activity.¹⁴

 

43- Reported the synthesis of 1-(substituted benzylidene)(N-sulphonyl hydrazino)-2-(N-methyl-phthalyl)- benzimidazole.⁴⁶

 

R=4-OH, 4-NO₂,

 

44- Reported the synthesis of novel Benzimidazole derivatives having antifungal activity.⁴⁷

45- Reported the synthesis novel Benzimidazole derivatives which shows antifungal activity against candida albicans,candida tropicalis, candida krusei, candida glabrata, Aspergillus fumigates.²²

R₁=2, 3-Cl C₆H₅O

R₂=H

R₃=CH₃

46- Reported the synthesis of 2-[3-(3,5,6-trichloro pyridine-2-yloxy)phenyl]-1-H-benzimidazole which shows antifungal activity.⁴⁸

 

R₁=H, Cl, NO₂, Br

47- Reported the synthesis of antifungal agents containing imidazole nucleus like clotriamazole, Miconazole, ketoconazole.⁴⁹

 

48- Reported the synthesis of 2-methyl and 2-amino benzimidazole derivatives which was evaluated against yeast saccharomyces cerevisiae.⁵⁰

 

 

49-Reported the synthesis of 5-(nitro/bromo)-styryl-2-benzimidazole derivatives having fungicidal activity.⁵¹

 

50- Reported the synthesis of novel benzimidazole derivatives which shows fungicidal activity against C.albicans.⁵²

 

R1	R2
-C3H7	H
-C3H7	F
	F

 

 

51- Reported the synthesis of methyl 5(6)-fluoro-6(5)-substituted-1-H-benzimidazole carbamate which shows antifungal activity.⁵³

 

R=Cl ,4-morpholinyl, 3-methyl piperidin-1yl

 

CONCLUSION:

Benzimidazole derivatives are well known to have various important pharmacological activities and are used for synthesis of a wide variety of medicinally active compounds. This review article summarizes the anti-bacterial and antifungal potential of Benzimidazole derivatives and the effect of substitutions of different groups on the anti-bacterial and antifungal activity. This summarized study is an attempt to bring about the anti-bacterial and antifungal for awaking the safe use of this important chemical moiety with minimal or no ulcerogenic effects in future.

 

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Received on 21.12.2013          Modified on 10.01.2014

Accepted on 18.01.2014         © RJPT All right reserved