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Available online at www.scholarsresearchlibrary.com
Scholars Research Library
Der Pharmacia Lettre, 2011, 3(2):284-291 (http://scholarsresearchlibrary.com/archive.html)
ISSN 0975-5071 USA CODEN: DPLEB4
Microwave assisted rapid and efficient synthesis, characterization and pharmacological evaluation of some novel benzimidazole assembled 1,5benzodizepine and 1,5-benzothiazepine derivatives
Janardan Singh Yadav and Y. K. Srivastava* Synthetic Organic Chemistry Laboratory, Department of Chemistry, M.P. Govt. P.G. College, Chittorgarh, Rajasthan (India) ______________________________________________________________________________ ABSTRACT Some 1,5 benzodizepines and 1,5 benzothiazepines have been synthesized employing microwave irradiation techniques and evaluated for their antimicrobial activities. 2- Acetyl benzimidazols (1) were reacted with appropriately substituted aromatic aldehydes (2) in the presence of base to furnish substituted chalcones (3a-f). These chalcones were further reacted with ortho phenylenediamine to offered 4-(1H-benzimidazol-2-yl)-2-phenyl-2,3-dihydro-1H-1,5benzodiazepines (4a-f). Reaction of the chalcones (3a-f) with 2- amino thiophenol yielded substituted 4-(1H-benzimidazol-2-yl)-2-phenyl-2,3-dihydro-1,5-benzothiazepines (5a-f). All the synthesized compounds were characterized by elemental analysis and IR, 1H NMR and Mass spectral data. All the compounds were screened for their antimicrobial activities against gram positive bacteria Staphylococcus aureus, Bacillus subtilis and gram negative bacteria Escherichia coli, Pseudomonas aeruginosa and fungal species like Candida albicans and Aspergillus niger organisms. Keywords: Microwave, Benzimidazole, Ortho phenylenediamine, 2-Amino thiophenol, Antimicrobials. ______________________________________________________________________________ INTRODUCTION Chalcones are important starting materials for the synthesis of various classes of heterocyclic compounds such as pyrazolines, isoxazolines, pyramidines, diazepines, benzodiazepines, benzothiazepines etc. Most of these compounds are highly bioactive and are widely used in pharmaceutics. The presence of enone function in the chalcone system is responsible for the bacteriostatic/bactericidal [1-3] activity.

Scholar Research Library

Y. K. Srivastava et al Der Pharmacia Lettre, 2011, 3(2):284-291 ______________________________________________________________________________ Some of the substituted chalcones and their derivatives have been reported to possess some interesting biological properties, which are detrimental to the growth of microbes [4], tubercle bacilli [5], malarial parasites [6], acrus [7], schistosoma and intestinal worms [8]. Benzodiazepines and their polycyclic derivatives are a very important class of bioactive compounds because of their pharmacological properties [9, 10]. Dizepines are useful as anticancer [11], antibacterial [12], psychotropic [13], antiemetic [14], anticonvulsant [15], herbicidal [16], muscle relaxant [17], antihypertensive [18], antidepressant [19], antiasthamatic [20], anti-inflammatory and bronchodilating agents [21]. Substituted 1,4 diezepine derivatives possess anti HIV activity [22] and antibacterial activity [23]. Benzodiazepines are well known CNS depressant compound and have emerged as an important area of research of treatment of traumatic conditions. 1,5 benzodizepines derivatives shows a large number of pharmacological properties such as they acted as sedatives [24], cerebrovasodilators [25], neuroleptics [26], antispasmodic [27], anticonvulsant [28], tranquilizing agents [29], antibacterial [30], psoriasis [31] and for treatment of smallpox [32]. Due to their wide range of biological activities, the synthesis of these compounds has received a great deal of attention. Some benzodiazepine derivatives are also used in industry, such as in photography, as dyes for acrylic fibers [33], and also as anti-inflammatory agents [34]. Due their wide range of pharmacological, industrial and synthetic applications, the synthesis of 1,5benzodiazepines has received considerable attention. Benzothiazepine derivatives are well known for diverse biological activities and play a key role as anticoagulant [35], diltiazem [36], antihypertensive [37] and antidepressant [38] compounds. The application of microwave irradiation in organic synthesis has attracted considerable attention in recent years and is becoming an increasingly popular technique [39]. The salient features of the microwave approach are rapid reaction rates, cleaner reaction products and enhanced yields [40-41]. Keeping the view of these observations and under the framework of Green Chemistry we herein report an environmentally benign synthesis of some novel benzodiazepine and benzothiazepine derivatives. MATERIALS AND METHODS Experimental: Starting material and reagents were procured from commercial chemical suppliers. All the chemicals and solvents used were of laboratory grade. Melting points were determined in open capillary tubes and are uncorrected. IR spectra (KBr, cm-1) were recorded on Perkin Elmer FTIR Spectrometer, 1H NMR(CDCl3 or DMSO-d6, ppm) spectra was recorded on a Brucker 300 MHz NMR spectrometer using TMS as an internal standard. Mass spectra(FAB, m/z %) were taken on Jeol-SX-600 Mass spectrometer using m-nitrobenzyl alcohol as matrix. The matrix peaks were observed at m/z 136,137,154,289 and 307. The purity of compounds and progress of the reaction was checked by TLC using silica gel-G as adsorbent. All the transformations were carried out in a domestic microwave oven (Samsung M1833N output 800 watt 2450 MHZ frequency).

Y. K. Srivastava et al Der Pharmacia Lettre, 2011, 3(2):284-291 ______________________________________________________________________________ The title compounds were prepared in the following steps: (A) Conventional process
(i) General procedure for synthesis of chalcones (3a-f)
2- Acetyl benzimidazole (0.01 mol) and appropriate aromatic aldehyde (0.012 mol) in ethanol were taken in a flask. Sodium hydroxide (40%; 10 ml) was added and the reaction mixture was refluxed on water bath for 4 to 5 hours then cooled at room temperature and poured in ice cold water further neutralized with dilute HCl. The product obtained was filtered and washed followed recrystallization from ethanol and acetone. The purity of the compounds were checked by TLC using silica gel G.
(ii) Synthesis of 4-(1H-benzimidazol-2-yl)-2-phenyl-2,3-dihydro-1H-1,5-benzodiazepines (4a-f)
A mixture of chalcone (3a-f) (0.01 mol) and ortho phenylenediamine (0.01 mole) in DMF (20 ML) was taken in conical flask to it catalytic amount of glacial acetic acid was added and mixture, refluxed on water bath for 9 to 10 hours, after completion of the reaction it was cooled to room temperature. The solid obtained was filtered and recrystallised from ethanol to give (4a-f).
(iii) Synthesis of 4-(1H-benzimidazol-2-yl)-2-phenyl-2,3-dihydro-1,5-benzothiazepines (5a-f)
An ultimate mixture of chalcone (3a-f) (0.01 mol) and 2-amino thiophenol (0.01 mole) in dry benzene (20 ML) was taken in conical flask to it catalytic amount of glacial acetic acid was added and mixture refluxed on water bath for 8 to 10 hours, and then cooled to room temperature. The solid separated was filtered and recrystallised from ethanol to give (5a-f). (B) Microwave assisted process
A solution of 2-acetyl benzimidazole (0.01 mol) and approximately aromatic aldehyde (0.012 mol) in ethanol were taken in beaker. Sodium hydroxide (40%, 10ml) was added to it. The reaction mixture was capped with a glass funnel and placed in microwave oven for 30 seconds to 3 minutes at 300 watts. It was then cooled to room temperature and poured in ice cold water containing with dilute HCl. The solid obtained was filtered and washed with water. It was recrystallized from ethanol-acetone mixture.

A mixture of chalcone (3a-f) (0.01 mol) and ortho phenylenediamine (0.01 mole) in DMF (10 ml) was taken in conical flask. To it glacial acetic acid in catalytic amount was added. The flask was capped with a glass funnel and subjected to MWI for 4.50 to 5.30 min. It was then cooled to room temperature. The solid separated was washed with water and recrystallized from ethanol to give (4a-f).
An ultimate mixture of chalcone (3a-f) (0.01 mol) and 2-amino thiophenol (0.01 mole) in dry benzene (10 ml) was taken in a conical flask. To it catalytic amount of glacial acetic acid was added and the mixture was subjected to microwave irradiation for 5 to 6 min. It was then cooled to room temperature. The solid separated was washed with water and recrystallized from ethanol to give (5a-f).
Y. K. Srivastava et al Der Pharmacia Lettre, 2011, 3(2):284-291 ______________________________________________________________________________ Characterization of newly synthesized compounds
(i) Characterization of synthesized compounds (3a-f)
1-(1H-benzimidazol-2-yl) -3- phenyl prop-2-en-1- one IR (KBr, cm-1): 3264-3444 (N-H str.), 3080 (C-H Str., Ar-H), 1667 (C=O Str.), 1597 (C=N Str.); 1H NMR (CDCl3, ppm): 9.32 (s, 1H, NH), 7.8-7.1 (m,9H, Ar-H), 5.6 (d,1H, =CH-Ar) 1-(1H-benzimidazol-2-yl) -3-(4- methoxy phenyl ) prop-2-en-1- one IR (KBr, cm-1): 3400 (N-H str.), 1654 (C=O Str.), 1575 (C=N Str.), 1088 (C=O Str.); 1H NMR (CDCl3, ppm): 9.08 (s, 1H, NH), 7.88-7.32 (m,8H, Ar-H), 5.57 (d,1H, =CH-Ar) 3.3(s,3H, OCH3). 1-(1H-benzimidazol-2-yl) -3-(4- cholorophenyl ) prop-2-en-1- one IR (KBr, cm-1): 3420 (N-H str.), 3050 (C-H Str. Ar-H), 1660 (C=O Str.), 1580 (C=N Str.), 770 (C-Cl); 1H NMR (CDCl3, ppm): 9.05 (s, 1H, NH), 7.84-7.30 (m,8H, Ar-H), 5.50 (d,1H, =CHAr). 1-(1H-benzimidazol-2-yl) -3-[4- (dimethylamino) phenyl] prop-2-en-1- one IR (KBr, cm-1): 3430 (N-H str.), 2913 (C-H Str., CH3), 1663 (C=O Str.), 1601 (C=NStr.); 1H NMR (CDCl3, ppm): 9.21 (s, 1H, NH), 7.79-7.27 (m,8H, Ar-H), 5.61 (d,1H, =CH-Ar) 3.19 (s,6H, N(CH3)2).
(ii) Characterization of synthesized compounds (4a-f)
4-(1H-benzimidazol-2-yl)-2-phenyl-2,3-dihydro-1H-1,5-benzodiazepine IR (KBr, max, cm-1): 3025 (Ar-H ), 1545 (C=N), 2930 (C-H), 3325(N-H); 1H NMR (CDCl3/DMSO-d6 , ppm): 8.65 (s,1H, NH), 7.20 (s,2H,>CH), 7.30-8.50 (18H, Aromatic). 4-(1H-benzimidazol-2-yl)-2-(4-methoxyphenyl)-2,3-dihydro-1H-1,5-benzodiazepine IR (KBr, max, cm-1): 3020 (Ar-H ), 1610 (C=N), 2935 (C-H), 3322(N-H), 1090 (O-C); 1H NMR (CDCl3/DMSO-d6 , ppm): 8.71 (s, 1H, NH), 7.20 (s,1H,>CH), 7.35-8.60 (17H, Aromatic), 3.79 (s,3H, OCH3). 4-(1H-benzimidazol-2-yl)-2-(4-chlorophenyl)-2,3-dihydro-1H-1,5-benzodiazepine IR (KBr, max, cm-1): 3030 (Ar-H ), 1585 (C=N), 2940 (C-H), 3345(N-H), 775 (C-Cl); 1H NMR (CDCl3/DMSO-d6 , ppm): 8.56 (s, 1H, NH), 7.15 (s,2H>CH), 7.22-8.45 (17H, Aromatic). 4-(1H-benzimidazol-2-yl)-2-(4- dimethylamino phenyl)-2,3-dihydro-1H-1,5-benzodiazepine IR (KBr, max, cm-1): 3045 (Ar-H ), 1600 (C=N), 2935 (C-H), 3330(N-H); 1H NMR (CDCl3/DMSO-d6 , ppm): 8.68 (s,1H, NH), 7.11 (s,1H,>CH), 7.25-8.50 (17H, Aromatic), 3.78 (s,6H, OCH3).

(iii) Characterization of synthesized compounds (5a-f)
4-(1H-benzimidazol-2-yl)-2-phenyl-2,3-dihydro-1,5-benzothiazepine IR (KBr, max, cm-1): 3075 (N-H ), 615 (C-S); 1H NMR (CDCl3/DMSO-d6 , ppm): 6.1(d,1H, C2H), 7.36 (d,1H,C3H), 6.07-7.17 (m,17H, Ar-H), 3.75 (s,1H,NH). 4-(1H-benzimidazol-2-yl)-2-(4-methoxyphenyl)-2,3-dihydro-1,5-benzothiazepine IR (KBr, max, cm-1): 3090 (N-H ), 612 (C-S); 1H NMR (CDCl3/DMSO-d6 , ppm): 6.16(d,1H, C2H), 7.38 (d,1H,C3H), 6.20-7.25 (m,16H, Ar-H), 3.76 (s,1H,NH), 3.95 (s,3H,OCH3). 287
Y. K. Srivastava et al Der Pharmacia Lettre, 2011, 3(2):284-291 ______________________________________________________________________________ 4-(1H-benzimidazol-2-yl)-2-(4-chlorophenyl)-2,3-dihydro-1,5-benzothiazepine IR (KBr, max, cm-1): 3080 (N-H ), 614 (C-S), 780 (C-Cl); 1H NMR (CDCl3/DMSO-d6 , ppm): 6.05(d,1H, C2H), 7.30 (d,1H,C3H), 6.08-7.27 (m,16H, Ar-H), 3.79 (s,1H,NH). 4-(1H-benzimidazol-2-yl)-2-(4- dimethylamino phenyl)-2,3-dihydro-1,5-benzothiazepine IR (KBr, max, cm-1): 3090 (N-H ), 615 (C-S),1110 (C-N); 1H NMR (CDCl3/DMSO-d6 , ppm): 6.14(d,1H, C2H), 7.37 (d,1H,C3H), 6.20-7.30 (m,16H, Ar-H), 3.75 (s,1H,NH), 2.45 (s,6H,N(CH3)2).
Figure 1, Scheme- 1: synthesis of 1,5-benzodiazepines &1,5-benzothiazepines
N N H R3 (1) NaoH MWI (2) O C CH3 R2 O

O C CH CH

R2 R1 R3

NH2 MWI NH2 MWI

R2 R1 N N H N NH R3 N H N S N
Y. K. Srivastava et al Der Pharmacia Lettre, 2011, 3(2):284-291 ______________________________________________________________________________ Antimicrobial activity All the synthesized compounds were tested for their antibacterial and antifungal activity in vitro by disc diffusion method, with gram positive bacteria S. aureus, B. subtilis and gram negative bacteria E. coli, P. aeruginosa and fungal species like C. albicans, A. niger organisms. Cifuroxacin HCl was used as a standard drug for antibacterial screening and fluconazole was used as a standard for antifungal screening. All the synthesized compound exhibited moderate antibacterial activities and significant antifungal activities. DMSO was used as a diluents which not effected the growth of microbes. The screening results have been tabulated in table 2.
Table 1-Physical and analytical characterization data of compounds (3a-f),(4a-f)&(5a-f). Compd 3a 3b 3c 3d 3e 3f 4a 4b 4c 4d 4e 4f 5a 5b 5c 5d 5e 5f R1 H OCH3 OCH3 OCH3 Cl N(CH3)2 H OCH3 OCH3 OCH3 Cl N(CH3)2 H OCH3 OCH3 OCH3 Cl N(CH3)2 R2 H H OCH3 OCH3 H H H H OCH3 OCH3 H H H H OCH3 OCH3 H H R3 H H H OCH3 H H H H H OCH3 H H H H H OCH3 H H Molecular Formula C16H12N2O C17H14N2O2 C18H16N2O3 C19H18N2O4 C16H11ClN2O C18H17N3O C22H18N4 C23H20N4O C24H22N4O2 C25H24N4O3 C22H17ClN4 C24H23N5 C22H17N3S C23H19N3OS C24H21N3O2S C25H23N3O3S C22H16ClN3S C24H22N4S Mol. Wt. MP c Analytical Characterization %C %N %O %S 77.41 11.29 06.45 73.38 10.07 11.51 70.12 09.09 15.58 67.45 08.28 18.93 68.08 09.92 05.67 74.22 14.43 04.49 78.10 16.56 75.00 15.21 04.34 72.36 14.07 08.04 70.09 13.08 11.21 70.96 15.05 75.59 18.37 74.36 11.83 09.01 71.68 10.90 04.15 08.31 69.39 10.12 07.71 07.71 67.41 09.43 10.78 07.19 67.86 10.79 08.22 72.36 14.07 08.04

Table 2- Antimicrobial study of synthesized compounds (4a-f) & (5a-f). Zone of inhibition in mm Antibacterial Activity Antifungal Activity Gram Positive Gram Negative S. aureus B. subtilis E. coli P. aeruginosa C. albicans A. niger 30 30
Comp,d 4a 4b 4c 4d 4e 4f 5a 5b 5c 5d 5e 5f S. Drug S. Drug
Ar Phenyl 4-methoxy phenyl 3, 4-dimethoxy phenyl 3,4,5 trimethoxy phenyl 4-chloro phenyl 4-dimethyl amino phenyl Phenyl 4-methoxy phenyl 3, 4-dimethoxy phenyl 3,4,5 trimethoxy phenyl 4-chloro phenyl 4-dimethyl amino phenyl Cifuroxacin HCl Fluconazole
Y. K. Srivastava et al Der Pharmacia Lettre, 2011, 3(2):284-291 ______________________________________________________________________________ RESULTS AND DISCUSSION Chalcones (3a-f) were prepared by both conventional and MWI method and were treated with ortho phenylenediamine to yielded 4-(1H-benzimidazol-2-yl)-2-phenyl-2,3-dihydro-1H-1,5benzodiazepines (4a-f). The chalcones on treatment with 2-amino thiophenol offered 4-(1Hbenzimidazol-2-yl)-2-phenyl-2,3-dihydro-1,5-benzothiazepines (5a-f) Scheme-1. The assigned structure and molecular formula of newly synthesized compounds (4a-f) & (5a-f) were confirmed on the basis of IR, 1H NMR and Mass spectral analysis. The compounds were screened for their antimicrobial activity in vitro. Physical and analytical characterization data of compounds (3a-f), (4a-f) & (5a-f) have been tabulated in table 1. CONCLUSION The Microwave Assisted method is a very efficient and selective protocol for Claisen Schmidt condensation of Chalcones. Operative simplicity, easy work-up procedure, better yields are other advantages of this method. The reaction was clean and the products were obtained in excellent yields. The synthesized compounds were identified by TLC, melting point & characterized by elemental analysis, IR, 1H NMR and Mass spectroscopy. The results obtained from this study confirmed that the product formed under microwave irradiation were better in yield and purity. The workup was easy. Acknowledgments The author are highly grateful to Dr. B.L. Verma (Retd. Peofessor, MLS University, Udaipur) for valuable suggestions, guidance and encouragement. Thanks are also due to the Director SAIF CDRI LUCKNOW and SAIF CHANDIGARH for spectral results and Dr. Kanika Sharma, Deptt. of Microbiology MLS University, Udaipur for antimicrobial activity. REFERENCES [1] Y. Kishimoto, Y. Akabori & T. Horiguchi, Chem Abstr, 1958,52, 13863b. [2] W.B.Geiger, J.E. Conn, J Am Chem. Soc., 1945,67,112. [3] E. Schraufstatter, Experientia, 1948,4 ,484. [4] D.H. Marrian, P.B. Russel & A.R. Todd, J. Chem Soc., 1947,1,419. [5] K. Yamaguchi, Y. Sakurai, M. Kurumi, Japanese Pat, 1972,72,47016. [6] F. Bayer, British Pat, 1954,708, 013. [7] D.W. Henry, U.S. Pat, 1973, 3, 726,920. [8] E. Velarde, Bol Soc Quim Peru, 1970,36, 127. [9](a) H. Schutz, Benzodiazepines, Springer, Heidelberg, 1982, 2,240. (b)R.K.Smalley, D. Barton and W. D. Ollis, Pergamon, Oxford, 1979, 4,600. (c) J. K. Landquist, A.R.Katritzkyand C.W.Rees, Pergamon, Oxford,1984, 1,166, 170. [10] L. O. Randall and B. Kappel, S. Garattini,E. Mussini and L. O. Randall, Raven Press, New York, 1973, 27. [11] I. Krezel, E. Mikiciuk-olisik, E. Zurek, and M.L. Glowka, Pharm Pharmacol. Commun, 1999, 5,485. [12] M. Antoine, M. Benequ, J.F. Desconclois, P.Giranel and G. Picaut, Chem. Abstr, 1991, 14, 143393. [13] S.J. Childress and M.I. Gluckman, J. Pharm. Sci, 1964,53,577. [14] Y. Hirokawa, H. Harada, T.Yoshikawa, N.Yashicle and S. Kato, Chem. Pharm. Bull, 2002,50,941. 290

 

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