SYNTHESIS, REACTIONS, AND PHARMACOLOGICAL APPLICATIONS OF 2-AMINOBENZIMIDAZOLES: AN UPDATE

Authors

  • Apeksha Motghare Department of Pharmaceutical Chemistry, Kamla Nehru College of Pharmacy, Butibori, Nagpur (MS), India.
  • Parimal Katolkar Department of Pharmaceutical Chemistry, Kamla Nehru College of Pharmacy, Butibori, Nagpur (MS), India.

DOI:

https://doi.org/10.22159/ajpcr.2022.v15i7.44899

Keywords:

2-Aminobenzimidazoles, Derivatives of 2-aminobenzimidazole, Pharmacological applications, Reactions

Abstract

Many drug molecules comprises of benzo fused heterocycles with two nitrogen atoms, that is, benzimidazole and its derivatives. Many biological active molecules contain that 2-aminobenzimidazole cores are among the foremost common structural components in medicinal chemistry. 2-aminobenzimidazole and its derivative have wide range of biological and pharmaceutical activities. In this review, the authors summarize synthesis, various chemical reactions, and biological activities of 2-aminobenzimidazole and its derivative.

Downloads

Download data is not yet available.

References

Rastogi R, Sharma S. 2-Aminobenzimidazoles in organic syntheses. Synthesis. 1983;1983:861-82. doi:10.1055/s-1983-30546.

2-Amino Benzimidazole. Available from: https://pubchem.ncbi. nlm.nih.gov/compound/2-Aminobenzimidazole. [Last accessed on 2021 Jun 10].

Stoermer M, Egan S, Forsyth CM, Moloney G. (Z)-N’-(1H-Benzo [d] imidazol-2-Yl)-Arylimidamide adducts of 2-aminobenzimidazole and aromatic nitriles: Structural and spectroscopic proof of regiochemical and stereochemical outcomes. Eur J Org Chem 2019;3: ???.

Azam M, Khan AA, Al-Resayes SI, Islam MS, Saxena AK, Dwivedi S, et al. Synthesis and characterization of 2-substituted benzimidazoles and their evaluation as anticancer agent. Spectrochim Acta A Mol Biomol Spectrosc 2015;142:286-91. doi:10.1016/j.saa.2015.01.106, PMID 25706598.

Pierron P. ???. Ann Chim Phys 1968;15:189.

Offenlegungssehrift D 2214600, Mar 25; 1972.

Stedman RJ, Inventor; SmithKline Corp, Assignee. 2-Aminobenzimidazole and A Process for Preparing 2-Aminobenzimidazoles. Vol. 3. United States Patent; 1969. p. 948.

Kiffer D, Levy R. A New synthetic method for 2-alkyl-2-aryl-and 2-Acylaminobenzimidazoles. CR Hebd Séances Acad Sci 1968;267:1730.

Omar AM, Amme O. Novel synthesis of 2-substituted aminobenzimidazoles from thiourea derivatives. The cyclodesulphurization of thio-compounds. Pharmazie 1972;27:798-9.

Omar AM, Ragab MS, Farghaly AM, Barghash AM. The cyclodesulphurization of thio-compounds. Part 12: A new simple method for the synthesis of N-alpha-substituted benzimidazoles from thiourea derivatives. Pharmazie 1976;31:348-50. PMID 959294.

Omar AM. The Cyclodesulfurization of thio-compounds; VII. A new facile synthesis of nα-substituted benzimidazoles. Synthesis 1974;1974:41-2. doi:10.1055/s-1974-23234.

Omar AM, El-Dine SH, Hazzaa A. ???. Pharmazie 1973;28:682.

Kiffer D. Cyclisation reaction of carbodiimides-study of conditions for synthesis of benzimidazoles. Bull Soc Chim Fr 1970;6:2377.

Stedman RJ. US Patent No. 3,455,948; 1969.

Griffin TS, Woods TS, Klayman DL. Thioureas in the synthesis of heterocycles. Adv Heterocycl Chem 1975;18:99-158. doi:10.1016/ S0065-2725(08)60129-4.

Murray JA, Dains FB. The action of amines on the esters of carboxy substituted ureas, thioureas and guanidines. III. J Am Chem Soc 1934;56:144-6. doi:10.1021/ja01316a044

Olin JF, Dains FB. The action of the halogen hydrins and of ethylene oxide on the thioureas. J Am Chem Soc 1930;52:3322-7. doi:10.1021/ ja01371a047.

Klopping HL. Chem Abstract. United States Patient, 2,933,502.

Klopping HL. Chemical Abstract. United States Patient 2,933,504.

Averkin EA, Beard CC, Dvorak CA, Edwards JA, Fried JH, Kilian JG, et al. Methyl 5 (6). J Med Chem 1975;18:1164-6. doi:10.1021/ jm00245a029, PMID 1177265.

McKellar QA, Scott EW. The benzimidazole anthelmintic agents-a review. J Vet Pharmacol Ther 1990;13:223-47. doi:10.1111/j.1365-2885.1990.tb00773.x, PMID 2231864.

Di HCi, HCi Di. Benzimidazoles- Table 1.89. Bisbenzimidazoles Compound Mp (C) Ref. Benzimidazoles and Cogeneric Tricyclic Compounds (1); 2009. p. 244.

Alaqeel SI. Synthetic approaches to benzimidazoles from o-phenylenediamine: A literature review. J Saudi Chem Soc 2017;21:229-37. doi:10.1016/j.jscs.2016.08.001

Adcock B, Lawson A, Miles DH. 2-Amino-2-imidazolines and 2-amino-2-oxazolines. J Chem Soc 1961;1014:5120-7.

Weiss S, Michaud H, Prietzel H, Krommer H. Neue, einfache synthese von 2‐aminobenzimidazol. Angew Chem 1973;85:866-7. doi:10.1002/ ange.19730851910.

Sawatari K, Mukai T, Suenobu K, Kamenozono S, Ika T. Chem Abstract Japanese Patent No. 76.16669; 1976. p. 63069.

Simonov AM, Anisimova VA. Synthesis and transformation of 2-aminobenzimidazoles (review). Chem Heterocycl Compd 1979;15:705-23. doi:10.1007/BF00473548.

Adams CD, Schlatter R. Chem [Abstract], 7.0057837. Republic of South Africa Patent No. 6706.589; 1968. p. 57837.

Adams CD, Schlatter R. Chem Abstr. 7.0012629; Republic of South Africa Patent No. 6906.326; 1970.

Craig PN, Hoover JR. InChem Abstract. British Patent No. 1111957. 1966. p. 1968-9.

Harsanyi K, Toth G, Simay A, Gonczi C, Takacs K. Hungarian Patent No. 5800.

Murphy DB, Picard JP. A Study of tautomerism in the 5-aminotetrazoles1. J Org Chem 1954;19:1807-14. doi:10.1021/jo01376a015

Sheverdina NI, Kocheshkov KA. Synthesis of primary amines by the reaction of-methylhydroxylamine with organomagnesium and organolithium compounds. Zh Obshch Khim 1938;8:1825-30.

Watkins DA. Benzimidazole pesticides: Analysis and transformations. Pestic Sci 1976;7:184-92. doi:10.1002/ps.2780070213.

Depost G, sillion B, salle R. Formation of 2-benzamidobenzimidazole, Study on its Thermal-stability. Comptes Rendus Hebdomadaires Seances Académie Des Sci Serie c; 1972. p. 697.

Ogura H, Kikuchi K. Heterocyclic compounds. XI. 1,3-Dipolar cycloaddition of benzimidazolium ylide with acetylenic compounds. J Org Chem 1972;37:2679-82.

Ogura H, Takayanagi H, Yamazaki Y, Yonezawa S, Takagi H, Kobayashi S, et al. Heterocyclic compounds. 10. Synthesis of some imidazo [1, 2-a] benzimidazoles with potent analgetic activities. J Med Chem 1972;15:923-6.

Lugosi P, Béla ÁG, Hornyák G. Synthesis and ring closure reactions of some N-(o-aminophenyl)-N-methyl-N’, N”-Disubstituted-guanidines and of N-(2-amino-4-methoxyphenyl)-N-methyl-N’-phenylthiourea. Period Polytech Chem Eng 1975;19:307-16.

Held P, Gross M. 2‐Dialkylamino‐benzimidazole aus O‐acylierten 1‐ Phenyl‐2‐hydroxy‐3, 3‐dialkylguanidinen. Z Chem 1973;13:292-3. doi:10.1002/zfch.19730130809.

Kirmse W. Reaktionen mit carbenen und iminen als zwischenstufen zur photochemischen und thermischen umwandlung organischer stickstoff‐verbindungen. Angew Chem 1959;71:537-41. doi:10.1002/ ange.19590711702.

Partridge MW, Turner HA. 430. Cyclic amidines. Part VII. Preparation of benziminazoles from N’-aryl-N-hydroxyamidines. J Chem Soc 1958;430:2086-92. doi:10.1039/JR9580002086.

Kalidhar U, Kaur A. An overview on some benzimidazole and sulfonamide derivatives with anti-microbial activity. J Pharm Biol Chem Sci 2011;2:1116-35.

Roche Y, Vigier J, Guyod JL, Boucherle A. Bull Trav Soc Pharm (Lyon) 1979;23, 27 CA; 1981. p. 42082.

Yutilov YM. Materially 4-oi[Chetvertoi] Nauchn. [Konf. Aspirantov]. Rostov-on-Don: Rostovsk. Univ.) Sb. 1962, 110; CA; 1964. p. 9262.

Martin D, Graubaum H, Esters C. Triazino‐benzimidazoles from 2‐ amino‐benzimidazole, aryl cyanates and carbonyl compounds. J Prakt Chem 1979;321:315-9.

Martin D, Graubaum H. German Patent (DDRP). C.A. 1980, 92; 1979. p. 136499.

Lalezari I, Nabahi S. Reaction of N‐cyanoformimidates with some heterocyclic compounds. A new synthesis of 5‐azaadenine and related compounds. J Heterocycl Chem 1980;17:1121-3. doi:10.1002/ jhet.5570170559.

Kikugawa Y. A facile N-alkylation of imidazoles and benzimidazoles. Synthesis. 1981;1981:124-5. doi:10.1055/s-1981-29356.

Murphy DB, Musco J. Methylation of 2-aminobenzimidazole. J Org Chem 1971;36:3469-70. doi:10.1021/jo00821a047.

Van Gelder JL, Raeymaekers AH, Roevens LF. German Patent. 2029637. 1971, CA; 1971. p. 100047.

Klopping HL. US CA Patent 2933504; 1960. p. 55.

Mayer KH, Lauer DH. Synthesis 1975;673.

Craig PN, Hoover JR. CA British Patent, No. 1111957; 1968. p. 96721.

Daun W, Scheinpflug H, Hamburger B. German Patent. 2140863, CA; 1973. p.124589.

Beard CC, US. CA Patent 3976654; 1966. p. 1977.

Rastogi R, Sharma S, Iyer RN. Synthesis of benzimidazole-2- carboxamides as potential anthelmintic agents. Indian J Chem 1979;18:464-7.

Khristich BI, Simonov AM, Suvorova GM. Khim. Geterotsikl Soedin 1293; CA; 1973. p. 146456.

Rastogi R, Sharma S, Iyer RN. ???. Eur J Med Chem 1979;14:489.

Paget CJ, Chamberlin JW, Wikel JH. CA Belgian Patent 851630; 1978. p. 170148.

Kuzmierkiewicz W, Tyczynska B. Schiff-bases of 2-aminobenzimidazole. Acta Pol Pharm 1980;37:39-42.

Augustin M, Kuppe KR. Cyclisierungsbreaktionen von 2-aminobenzimidazolen zu s-triazino [1, 2-a] benzimidazolen. Tetrahedron 1974;30:3533-8. doi:10.1016/S0040-4020(01)97537-4.

Dashkevich LB, Korbelainen ES. Khim. Geterotsikl Soedin, No. 37836 CA; 1967. p. 37836.

Bajwa JS, Sykes PJ. New steroidal heterocycles: Androstano [3, 2-b](pyrimido [1, 2-a] benzimidazoles). J Chem Soc Perkin Trans 1980;1:1859-61.

Basaglia L, Mariani B. ???. Ann Chim (Rome) 1963;53:755.

Eicher T, Franke G. Zur reaktion von diphenylcyclopropenon mit guanidinen. Liebigs Ann Chem 1981;1981:1337-53. doi:10.1002/ jlac.198119810802.

Antaki H, Petrow V. 119. New syntheses of heterocyclic compounds. The condensation of ethyl β-aminocrotonate with some cyclic amidines-Part XII. J Chem Soc 1951:551-5.

Elnagdi MH, Wamhoff H. A novel synthesis of azolopyrimidines. Chem Lett 1981;10:419-22. doi:10.1246/cl.1981.419.

Crippa GB, Perroncito G, Sacchetti G. Gazz Chim Ital; CA; 1935. p. 4007.

Simonov AM, Koshchienko YV, Suvorova GM, Tertov BA, Malysheva EN. Khim. Geterotsikl Soedin; 1976. p. 72521.

Chow AW, Jakas DR, Trotter BP, Hall NM, Hoover JR. Reaction of 2‐aminobenzimidazole with bifunetional carboxylie acid derivatives. Formation of pyrimido [1, 2‐a] benzimidazolones. J Heterocycl Chem 1973;10:71-5. doi:10.1002/jhet.5570100116.

Trachenko PV, Simonov AM, Popov II. Khim. Geterotsikl Soedin; 1978. p. 190727.

Simonov AM, Borisova TA. U.S.S.R. Patent, 478007. CA; 1976. p. 17339.

Schulze W, Letsch G. Potential nitrogen lost transport forms. Bis-(beta-chlorethyl)-carbamoylderivatives of benzimidazolones, benzimidazolthiones and benzimidazolonimides. Pharmazie 1973;28:367-71.

Krichovskaya AA, Mendzneritskaya LG, Butko VV. Oksibioticheskie Anoksibioticheskie protsessy Eksp. Klin Patol 1975;115:87321.

Dransch G, Hoerlein G. German Patent. (Dos) 2250469. CA; 1974. p. 13512.

Tunçbilek M, Kiper T, Altanlar N. Synthesis and in vitro antimicrobial activity of some novel substituted benzimidazole derivatives having potent activity against MRSA. Eur J Med Chem 2009;44:1024-33. doi:10.1016/j.ejmech.2008.06.026, PMID 18718694.

Simonov AM, Po O, Azolov K. (Rostov-On Don State University, U.S.S.R.); 1965.

Olbe LE, Carlsson E, Lindberg P. A proton-pump inhibitor expedition: The case histories of omeprazole and esomeprazole. Nat Rev Drug Discov 2003;2:132-9. doi:10.1038/nrd1010, PMID 12563304.

Bywater WG, McGinty DA, Jenesel ND. Antithyroid studies: II. The goitrogenic activity of some imidazoles and benzimidazoles. J Pharmacol 1945;85:14-22.

Vonder CJ, Frey C. Swiss Patent 613465. CA; 1980. p. 43279.

Published

07-07-2022

How to Cite

Motghare, A., and P. Katolkar. “SYNTHESIS, REACTIONS, AND PHARMACOLOGICAL APPLICATIONS OF 2-AMINOBENZIMIDAZOLES: AN UPDATE”. Asian Journal of Pharmaceutical and Clinical Research, vol. 15, no. 7, July 2022, pp. 35-46, doi:10.22159/ajpcr.2022.v15i7.44899.

Issue

Section

Review Article(s)