Volume 6, Issue 5, October 2018, Page: 83-94
A Review on Heterocyclic: Synthesis and Their Application in Medicinal Chemistry of Imidazole Moiety
Mossaraf Hossain, Department of Chemistry, University of North Bengal, Darjeeling, India; Department of Chemistry, Siliguri College, Darjeeling, India
Ashis Kumar Nanda, Department of Chemistry, University of North Bengal, Darjeeling, India
Received: Oct. 18, 2018;       Accepted: Nov. 1, 2018;       Published: Nov. 28, 2018
DOI: 10.11648/j.sjc.20180605.12      View  19      Downloads  30
Abstract
In an organic chemistry, largest families of organic compounds are belongs in the heterocyclic compounds. In our daily life important of heterocyclic compounds are of very essential. It has broad range of application in medicinal chemistry and in agrochemicals products. Applications are also found in as developers, as corrosion inhibitors, sanitizers, as copolymers, antioxidants, dye stuff. There is always an important thing about an efficient methodology for synthesizing of new heterocycles moiety. Now in literature survey reveals that more than 85-95% new drugs containing heterocycles which has bright scientific insight in the biological system. In this review work, I mainly focus such type of heterocycle and their families which has main utility in medicinal chemistry. In the recent past developments of imidazole-based compounds in the wide range of medicinal chemistry such as antihypertensive, antineuropathic, antitubercular, antiviral, anti-inflammatory, antibacterial, antiobesity, antiparasitic, antifungal, antihistaminic, anticancer, and other potential medicinal agents with their broad applications in pathology and diagnostics. Derivatives of imidazole have placed a unique position in the medicinal chemistry field. The involvement of the imidazole scaffold is a key of synthetic strategy in the drug discovery system. The imidazole moiety is a part of several important naturally occurring products, including histamine, purine, nucleic acid and histidine. It is expected that this brief review could be attractive for new thoughts from academia and pharmaceutical industries to designs of more biologically active and non-toxic imidazole-based drugs. The aims of this review work to the reported imidazole derivatives with pharmaceuticals activity during the past years.
Keywords
Heterocyclic, Imidazole, Anti-Cancer, Anti-Bacterial, Anti-Hypertensive, Anti-Inflammatory
To cite this article
Mossaraf Hossain, Ashis Kumar Nanda, A Review on Heterocyclic: Synthesis and Their Application in Medicinal Chemistry of Imidazole Moiety, Science Journal of Chemistry. Vol. 6, No. 5, 2018, pp. 83-94. doi: 10.11648/j.sjc.20180605.12
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Copyright © 2018 Authors retain the copyright of this article.
This article is an open access article distributed under the Creative Commons Attribution License (http://creativecommons.org/licenses/by/4.0/) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
Reference
[1]
A. Gomtsyan. Heterocycles in drugs and drug discovery. Chem. Heterocycl. Compd. 2012, 48: 7–10.
[2]
H. B. Broughton, I. A. Watson. Selection of Heterocycles for drug design. J. Mol. Graph. Model. 2004, 23: 51–58.
[3]
M. S. Salem, Sakr, S. I. El-Senousy, W. M. Madkour, H. M. F. Synthesis, Antibacterial, and Antiviral Evaluation of New Heterocycles Containing the Pyridine Moiety. Arch. Pharm. (Weinheim). 2013, 346: 766–773.
[4]
N. M. A. El-salam, M. S. Mostafa, G. A. Ahmed, O. Y. Alothman. Synthesis and Antimicrobial Activities of Some New Heterocyclic Compounds Based on 6- Chloropyridazine-3 (2H) –thione. J. Chem. 2013, 13: 1–8.
[5]
M. E. Azab, M. M. Youssef, E. A. El-Bordany. Synthesis and Antibacterial Evaluation of Novel Heterocyclic Compounds Containing a Sulfonamido Moiety. Molecules 2013, 18: 832–844.
[6]
E. R. El-Sawy, M. S. Ebaid, H. M. Abo-Salem, A. H. Al-Sehemi, A. G. Mandour. Synthesis, anti-inflammatory, analgesic and anticonvulsant activities of some new 4,6- dimethoxy-5- (heterocycles)benzofuran starting from naturally occurring visnagin. Arab. J. Chem. 2013, 7: 914–923.
[7]
X. Cao, Z. Sun, Y. Cao, R. Wang, T. Cai, W. Chu, W. Hu, Y. Yang. Design, Synthesis, and Structure–Activity Relationship Studies of Novel Fused Heterocycles-Linked Triazoles with Good Activity and Water Solubility. J. Med. Chem. 2014, 57: 3687–3706.
[8]
Y. Chen, K. Yu, N. Y. Tan, R. H. Qiu, W. Liu, N. L. Luo, L. Tong, C. T. Au, Z. Q. Luo, S. F. Yin. Synthesis, characterization and anti-proliferative activity of heterocyclic hypervalentorganoantimony compounds. Eur. J. Med. Chem. 2014, 79: 391–398.
[9]
E. R. El-Sawy, A. H. Mandour, El-Hallouty, S. M. Shaker, K. H. H. M. Abo-Salem. Arab. J. Chem. 2013, 6: 67–78.
[10]
Mabkhot, Y. N. Barakat, A. Al-Majid, A. M. Alshahrani, S. Yousuf, M. I. S. Choudhary. Synthesis, reactions and biological activity of some new bis-heterocyclic ring compounds containing sulphur atom. Chem. Cent. J. 2013, 7: 112–120.
[11]
D. A. Williams and T. L. Lemke. Foye’s Principles of medicinal chemistry, Lippincott Williams and Wilkins, 2002, 5: 36.
[12]
S. N. PandeyaNath. A Text Book of medicinal chemistry. SG publisher, 2004, 1(3): 2-3.
[13]
H. Singh and V. K. Kapoor. Medicinal and Pharmaceutical Chemistry. Vallabh Prakashan, 2008, 2: 1 -2.
[14]
D. Lednicer, L. A. Mitscher. In Organic Chemistry of Drug Synthesis. Wiley IntersciencnewYork, 1997, 1: 226.
[15]
E. G. Brown. Ring Nitrogen and Key Biomolecules. Kluwer Academic Press, 1998.
[16]
A. R. KatritzkyRees. Comprehensive Heterocyclic Chemistry, 1984, 5: 469-498.
[17]
M. Grimmett, Ross. Imidazole and Benzimidazole Synthesis. Academic Press, 1997.
[18]
A. F. Pozharskii, et al. Heterocycles in Life and Society. John Wiley & Sons, 1997.
[19]
C. Congiu, M. T. Cocco and V. Onnis. Design, synthesis, and in vitro antitumor activity of new 1,4-diarylimidazole-2-ones and their 2-thione analogues. Bioorganic& Medicinal Chemistry Letters.2008, 18: 989–993.
[20]
Heterocyclic Chemistry TL Gilchrist, the Bathpress 1985 ISBN 0-582-01421-2.
[21]
A. M. Venkatesan, A. Agarwal, T. Abe, H. O. Ushirogochi, D. Santos, Z. Li, G. Francisco, Y. I. Lin, P. J. Peterson, Y. Yang, W. J. Weiss, D. M. Shales, T. S. Mansour. 2-(4-Chloro­phen­yl)-4,5-diphenyl-1-(prop-2-en-1-yl)-1H-imidazole. Bioorg. Med. Chem. 2008, 16: 1890–1902.
[22]
M. Su Han and D. H. Kim. Synthesis of Novel Imidazoles as Potent Antimicrobial Agents. Bioorganic & Medicinal Chemistry Letters. 2001, 11: 1425-1427.
[23]
T. Nakamura, H. Kakinuma, H. Umemiya, H. Amada, N. Miyata, K. Taniguchi, K. Bando and M. Sato. Imidazole derivatives as new potent and selective 20-HETE synthase inhibitorsBioorganic& Medicinal Chemistry Letters. 2004, 14: 333–336.
[24]
M. A. Bbizhayev, Life Sci., 2006, 78: 2343–2357.
[25]
G. Roman, J. G. Riley, J. Z. Vlahakis, R. T. Kinobe, J. F. Brien, K. Nakatsu, W. A. Szarek. Hemeoxygenase inhibition by 2-oxy-substituted 1-(1H-imidazol-1-yl)-4-phenylbutanes: Effect of halogen substitution in the phenyl ring Bioorg. Med. Chem. 2007, 15: 3225–3234.
[26]
J. L. Adams, J. C. Boehm, T. F. Gallagher, S. Kassis, E. F. Webb, Ralph Hall, Margaret Sorenson, Ravi Garigipati, Don E. Griswold and John C. Lee. Pyrimidinylimidazole inhibitors of p38: cyclic N-1 imidazole substituents enhance p38 kinase inhibition and oral activity. Bioorg. Med. Chem. Lett. 2001, 11: 2867-2870.
[27]
P. G. Nantermet, J. C. Barrow, S. R. Lindsley, M. Young, S. Mao, S. Carroll, C. Bailey, M. Bosserman, D. Colussi, D. R. McMasters, J. P. Vacca, H. G. Selnick. Imidazole acetic acid TAFIa inhibitors: SAR studies centered around the basic P1′ group. Bioorg. Med. Chem. Lett. 2004, 14: 2141–2145.
[28]
K. Bhandari, N. Srinivas, G. B. S. Keshava, P. K. Shukla. Tetrahydronaphthyl azole oxime ethers: The conformationally rigid analogues of oxiconazole as antibacterials. Eur. J. Med. Chem., 2009, 44: 437-447.
[29]
S. Emami, A. Foroumadi, M. Falahati, E. Lotfali, S. Rajabalian, d S Ahmed Ebrahimi, S. Farahyarc and A. Shafiee. 2-Hydroxyphenacyl azoles and related azolium derivatives as antifungal agents. Bioorganic & Medicinal Chemistry Letters. 2008, 18: 141–146.
[30]
R. K. Ujjinamatada, A. Baier, P. Borowski, R. S. Hosmane. An analogue of AICAR with dual inhibitory activity against WNV and HCV NTPase/helicase: Synthesis and in vitro screening of 4-carbamoyl-5-(4,6-diamino-2,5-dihydro-1,3,5-triazin-2-yl)imidazole-1-β-d-ribofuranoside. Bioorg. Med. Chem. Lett. 2007, 17: 2285–2288.
[31]
R. V. Shingalapur, K. M. Hosamani, R. S. Keri. Synthesis and evaluation of in vitro anti-microbial and anti-tubercular activity of 2-styryl benzimidazoles. European Journal of Medicinal Chemistry. 2009, 44: 4244–4248.
[32]
M. Kidwai, P. Mothsra, V. Bansal, R. K. Somvanshi, A. S. Ethayathulla, S. Dey and T. P. Singh. One-pot synthesis of highly substituted imidazoles using molecular iodine: A versatile catalyst. Journal of Molecular catalyst A. 2007, 265: 177-182.
[33]
S. Sharma, S. Gangal and A. Rauf. Convenient one-pot synthesis of novel 2-substituted benzimidazoles, tetrahydrobenzimidazoles and imidazoles and evaluation of their in vitro antibacterial and antifungal activities. European Journal of Medicinal Chemistry. 2009, 44: 1751-1757.
[34]
J. Pandey, V. K. Tiwari, S. S. Verma, V. Chaturvedi, S. Bhatnagar, S. Sinha, A. N. Gaikwad and R. P. Tripathi. Synthesis and antitubercular screening of imidazole derivatives. European Journal of Medicinal Chemistry. 2009, 44: 3350-3355.
[35]
A. Hasaninejad, A. Zare, M. Shekouhy and J. A. Rad. Catalyst-Free One-Pot Four Component Synthesis of PolysubstitutedImidazoles in Neutral Ionic Liquid 1-Butyl-3-methylimidazolium Bromide. J. Comb. Chem. 2010, 12: 844-849.
[36]
C. Mukhopadhyay, P. K. Tapaswi and M. G. B. Drew. Room temperature synthesis of tri-, tetrasubstitutedimidazoles and bis-analogues by mercaptopropylsilica (MPS) in aqueous methanol: application to the synthesis of the drug trifenagrel. Tetrahedron Letters. 2010, 51: 3944-3950.
[37]
H. R. ShaaterianandM. Ranjban. An environmental friendly approach for the synthesis of highly substituted imidazoles using Brønsted acidic ionic liquid, N-methyl-2-pyrrolidonium hydrogen sulfate, as reusable catalyst. Journal of Molecular Liquids. 2011, 160: 40-49.
[38]
Zhong-JianCai, Shun-Yi Wang and Shun-Jun Ji. CuI/BF3·Et2O Cocatalyzed Aerobic Dehydrogenative Reactions of Ketones with Benzylamines: Facile Synthesis of Substituted Imidazoles. Org. Lett. 2012, 14(23): 6068-6071.
[39]
Dong Tang, Ping Wu, Xiang Liu, Yong-Xin Chen, Shuai-Bo Guo, Wen-Lin Chen, Jia-Gen Li, and Bao-Hua Chen. Synthesis of MultisubstitutedImidazoles via Copper-Catalyzed [3 + 2] Cycloadditions. J. Org. Chem., 2013, 78 (6), pp 2746–2750.
[40]
Chung-Yu Chen, Wan-Ping Hu, Pi-Cheng Yan, GopalChandruSenadi, and Jeh-Jeng Wang. Metal-Free, Acid-Promoted Synthesis of Imidazole Derivatives via a Multicomponent Reaction. Org. Lett. 2013, 15 (24): 6116–6119.
[41]
Ahmad Reza, Moosavi-Zare, ZhilaAsgari, Abdolkarim Zare, Mohammad Ali Zolfigol and Mohsen Shekouhy. One pot synthesis of 1,2,4,5-tetrasubstituted-imidazoles catalyzed by trityl chloride in neutral media. RSC Adv. 2014,4:60636-60639.
[42]
IftikharAhsan, K. K. Sharma, Arun Sharma, Suroor Ahmed Khan and Uzma Khan. Design and synthesis of some imidazole derivatives containing 2-(4- chlorophenyl)-4, 5-diphenyl imidazole moiety as anti-inflammatory and antimicrobial agents. Der PharmaChemica. 2014, 6 (3): 320-325.
[43]
Tarun Kumar, DeeptiVerma, Rubem F. S. Menna-Barreto, Wagner O. Valença, Eufrânio N. da Silva JúniorandIrishi N. N. Namboothiri. Synthesis of imidazoles via cascade reaction of nitroallylic acetates with amidines and studies on their trypanocidal activity. Org. Biomol. Chem. 2015, 13: 1996-2000.
[44]
Yuelu Zhu, Cheng Li, Jidong Zhang, Mengyao She, Wei Sun, Kerou Wan, Yaqi Wang, Bin Yin, Ping Liu, and Jianli Li. A Facile FeCl3/I2-Catalyzed Aerobic Oxidative Coupling Reaction: Synthesis of TetrasubstitutedImidazoles from Amidines and Chalcones. Org. Lett:2015, 17 (15): 3872–3875.
[45]
Jingjing Zhang, QingheGao, Xia Wu, Xiao Geng, Yan-Dong Wu and Anxin Wu. Dual Roles of Methyl Ketones in Radziszewski-Type Reaction: Formal [2 + 1 + 1 + 1] Synthesis of 1,2,5-Trisubstituted Imidazoles. Org. Lett. 2016, 18 (7): 1686–1689.
[46]
K. Pradhan, B. K. Tiwary, M. Hossain, R. Chakraborty, A. K. Nanda. A mechanistic study of carbonyl activation under solvent-free conditions drawn from the synthesis of imidazoles. RSC Adv. 2016,6: 10743-10749.
[47]
E. Vessally, S. Soleimani-Amiri, A. Hosseinian, L. Edjlalid and A. Bekhradnia. New protocols to access imidazoles and their ring fused analogues: synthesis from N-propargylamines. RSC Adv. 2017, 7: 7079–7091.
[48]
M. Hossain, K. Pradhan and A. K. Nanda. An expeditious synthetic protocol for chlorination of imidazole N-oxide: Synthesis of 2-chloroimidazoles. Tetrahedron Letters. 2017, 58: 3772–3776.
[49]
R. Thomas, M. Hossain, Y. Sheena Mary, K. S. Resmi, S. Armakovic, S. J. Armakovic, A. K. Nanda, V. K. Ranjan, G. Vijayakumar and C. Van Alsenoy. Spectroscopic analysis and molecular docking of imidazole derivatives and investigation of its reactive properties by DFT and molecular dynamics simulations. Journal of Molecular Structure. 2018, 1158: 156-175.
[50]
M. Smitha, Y. Sheena Mary, M. Hossain, K. S. Resmi, S. Armakovic, S. J. Armakovic, R. Pavithran, A. K. Nanda and C. Van Alsenoy. Two novel imidazole derivatives - Combined experimental and computational study. Journal of Molecular Structure. 2018, 1173: 221-239.
[51]
K. C. S. Achar, K. M. Hosamani, H. R. Seetharamareddy. In-vivo analgesic and anti-inflammatory activities of newly synthesized benzimidazole derivatives. European Journal of Medicinal Chemistry. 2010, 45; 2048–2054.
[52]
A. Puratchikody and M. Doble. Antinociceptive and antiinflammatory activities and QSAR studies on 2-substituted-4,5-diphenyl-1H-imidazoles. Bioorganic & Medicinal Chemistry. 2007, 15: 1083–1090.
[53]
D. Sharma, B. Narasimhan, P. Kumar, V. Judge, R. Narang, E. De Clercq, J. Balzarini. Synthesis, antimicrobial and antiviral evaluation of substituted imidazole derivatives. European Journal of Medicinal Chemistry. 2009, 44: 2347–2353.
[54]
R. V. Shingalapur, K. M. Hosamani, R. S. Keri. Synthesis and evaluation of in vitro anti-microbial and anti-tubercular activity of 2-styryl benzimidazoles. European Journal of Medicinal Chemistry. 2009, 44: 4244–4248.
[55]
D. Zampieri, M. G. Mamolo, L. Vio, E. Banfi, G. Scialino, M. Fermeglia, M. Ferrone and S. Pricl. Synthesis, antifungal and antimycobacterial activities of new bis-imidazole derivatives, and prediction of their binding to P45014DM by molecular docking and MM/PBSA method. Bioorganic & Medicinal Chemistry. 2007, 15: 7444–7458.
[56]
D. Olender, J. Zwawiak, V. Lukianchuk, R. Lesyk, A. Kropacz, A. Fojutowski, L Zaprutko. Synthesis of some N-substituted nitroimidazole derivatives as potential antioxidant and antifungal agents. European Journal of Medicinal Chemistry. 2009, 44:645-652.
[57]
F. Hadizadeh, H. Hosseinzadeh, V. Sadat Motamed-Shariaty, M. Seifi and S. Kazemi, Synthesis and Antidepressant Activity of N-Substituted Imidazole-5-Carboxamides in Forced Swimming Test Model. Iranian Journal of Pharmaceutical Research. 2008, 7(1): 29-33.
[58]
P. Gupta, S. Hameed, R. Jain. Ring-substituted imidazoles as a new class of anti-tuberculosis agents. European Journal of Medicinal Chemistry. 2004, 39: 805– 814.
[59]
P. jyoti, T. K. Vinod, V. S. Shyam, C. Vinita, S. Bhatnagar, S Sinha, A. N. Gaikwad and R. P. Tripathi. Synthesis and antitubercular screening of imidazole derivatives. European Journal of Medicinal Chemistry. 2009, 44: 3350-3355.
[60]
M. Tonelli, M. Simone, B. Tasso, F. Novelli, V. Boido. Antiviral activity of benzimidazole derivatives. II. Antiviral activity of 2-phenylbenzimidazole derivatives. Bioorganic & Medicinal Chemistry. 2010, 18: 2937–2953.
[61]
K. Bhandari, N. Srinivas, V. K. Marrapu, A. Verma, S. Srivastava, S. Gupta. Synthesis of substituted aryloxy alkyl and aryloxy aryl alkyl imidazoles as antileishmanial agents. Bioorganic & Medicinal Chemistry Letters. 2010, 20:291–293.
[62]
Y. Özkay, I. Iskar, Z. Incesu, G. e. Akalın. European Journal of Medicinal Chemistry. 2010, xxx: 1-9.
[63]
H. M. Refaat. Synthesis and anticancer activity of some novel 2-substituted benzimidazolederivativesEuropean Journal of Medicinal Chemistry. 2010, 45:2949-2956.
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