2
How to cite this paper
APA: Nirwan, N., Pareek, C & Swami, V. (2020). Indolylimidazoles: Synthetic approaches and biological activities. Current Chemistry Letters, 9(1), 31-50.
Chicago/Turabian: Nirwan, N., Pareek, C & Swami, V. 2020. "Indolylimidazoles: Synthetic approaches and biological activities." Current Chemistry Letters 9, no. 1 (2020): 31-50.
AMA: Nirwan, N., Pareek, C & Swami, V. Indolylimidazoles: Synthetic approaches and biological activities. Current Chemistry Letters. 2020;9(1):31-50.
References
1 Kawasaki I., Katsuma H., Nakayama Y., Yamashita M. Y., & Ohta S. (1998) Total Synthesis of Topsentin, Antiviral and Antitumor Bis(indolyl)imidazole. Heterocycles, 48 (9) 1887-1901.
2 Burres N. S., Barber D. A., Gunasekera S. P., Shen L.L., & Clement J. J. (1991) Antitumor activity and biochemical effects of Topsentin. Bio. Pharm., 42(4) 745-751.
3 Bartik K., Braekman J. C., Daloze D., Stoller C., Huysecom J., Vandevyver G., et al. (1987) Topsentins, new toxic bis-indole alkaloids from the marine sponge Tepsentiagenitrix. Canadian J. of Chem., 65(9) 2118–2121.
4 Morris S. A., & Andersen R. J. (1990) Brominated bis(indole) alkaloids from the marine sponge hexadella sp. Tetrahedron, 46(3) 715–720.
5 Sakemi S., & Sun H. H. (1991) Nortopsentins A, B, and C., Cytotoxic and antifungal imidazolediylbis[indoles] from the sponge Spongosoritesruetzleri. J. of Org. Chem., 56(13) 4304–4307.
6 Bao B., Sun Q., Xinsheng Y., Hong J., Lee C. O., Sim C. et al. (2005) Cytotoxic bisindole alkaloids from a marine sponge Spongosorites sp. J. of Nat. Prod., 68(5) 711–715.
7 Tsujii S., Rinehart K. L., Gunasekera S. P., Kashman Y., Cross S. S., Lui M. S., et al. ( 1988) Topsentin, bromotopsentin, and dihydrodeoxybromotopsentin: antiviral and antitumorbis(indolyl) imidazoles from Caribbean deep-sea sponges of the family Halichondriidae, Structural and synthetic studies. J. of Org. Chem., 53(23) 5446-5453.
8 Shin J., Seo Y., Cho K. W., Rho J. R., & Sim C. J. (1999) New bis(indole) alkaloids of the topsentin class from the sponge Spongosoritesgenitrix. J. of Nat. Prod., 62(4) 647– 649.
9 Casapullo A., Bifulco G., Bruno I. and Riccio R. (2000) New Bisindole Alkaloids of the Topsentin and Hamacanthin Classes from the Mediterranean Marine Sponge Rhaphisialacazei. J. of Nat. Prod., 63(4) 447–451.
10 McConnell O. J., Saucy. G., & Jacobs R. (1994). US Patent 5,290,777.
11 Wright A. E., Pomponi S. A., & Roberts J. A. (1999). Patent WO 9,942,092.
12 Sakemi, S., & Sun, H. H. (1991). Nortopsentins A, B, and C. Cytotoxic and antifungal imidazolediylbis [indoles] from the sponge Spongosorites ruetzleri. J. of Org. Chem., 56(13), 4304-4307.
13 Alvarado S., Roderts B. F., Wright A. E., & Chakrabarti D. (2013) The Bis(Indolyl)Imidazole Alkaloid Nortopsentin-A Exhibits Antiplasmodial Activity. Antimicrobial Ag. and Chemo., 57(5) 2362–2364.
14 Bewely C. A., & Faulkner D. J. (1998) Lithistid sponges: Star performers or hosts to the stars. Angewandte Chem. International Ed. in Eng., 37(16) 2162-2178.
15 Hogan I. T., & Sainsbury M. (1984) The synthesis of dendrodoine, 5-[3-(N,N-dimethylamino-1,2,4-thiadiazolyl]-3-indolylmethanone, a metabolite of the marine tunicate dendroda grossular. Tetrahedron, 40(4) 681-682.
16 Capon R. J., Peng C., & Dooms C. (2008) Trachycladindoles A-G: Cytotoxic heterocycles from an Australian marine sponge, Trachycladuslaevispirulifer. Org. & Biomo. Chem., 6(15) 2765-2771.
17 Hlasta D. J. (1991). US patent 5,017,584. Chem. Abstr., 115, 232,249.
18 Karabelas K., Lepisto M., & Sjo P. (2000). Word patent WO 2,000,078,750. Chem. Abstr., 13, 471,594.
19 Karabelas K., Lepisto M., & Sjo, P. (1999). Word patent WO 9,932,483. Chem. Abstr., 13, 158,823.
20 Levy, L. (1977) Proceedings, Soc. Exp. Biol. Med., 153 34-36. Chem. Abstr., 8,625,978.
21 Hoff, D. R. (1970). DE. 1,962,822. Chem. Abstr., 7,387,931.
22 Sato, H., Tsuda, M., Watanabe, K., & Kobayashi, J. (1998) Rhopaladins A-D, new indole alkaloids from marine tunicate Rhopalaea sp. Tetrahedron, 54(30) 8687-8690.
23 Doemling A., & Beck B. (2001). Word patent WO 2001,025,213. Chem. Abstr., 134,295,819.
24 Reddy Y. T., Konjeti R. S., Nidhish S., Reddy P. N., Freeman M. L., & Peter A. C. (2010) Novel substituted (Z)-5-((N-Benzyl-1H-indol-3-yl)methylene)imidazolidine-2,4-diones and 5-((N-Benzyl-1H-indol-3-yl)methylene)pyrimidine-2,4,6(1H,3H,5H)-triones as Potent Radio-sensitizing Agents. Bioorg. and Medi. Chem. Lett., 20(2) 600-602.
25 Roffey J. R. A. (1996) The Synthesis of Indole Containing Anticancer Compounds, PhD thesis, Loughborough University, UK.
26 Zoraghi R., Worrall L., See R. H., Strangman W., Popplewe W. L., Gong H., et al. (2011) MRSA Pyruvate Kinase as a Target for Bis-indole Alkaloids with Antibacterial Activities. J. of Bio. Chem., 286(52) 44716-44725.
27 Singh P., Kumar R., Tiwari S., Khanna R. S., Tewari A. K., Khanna H. D., et al. (2015) Docking, Synthesis and Evaluation of Antioxidant Activity of 2,4,5-Triaryl Imidazole. Clini. & Medi. Biochem., 1(1) 1-4.
28 Hilya V. P., Grishko L. G., Golubushina G. M., Arkhipova N. N. and Turov A. V. (1994) Khim. Geterotsikl. Soedin., 1063-1070. Chem., Abstr. 122,314,495.
29 Rajaramana D., Sundararajana G., Loganathb N. K., & Krishnasamya K. (2017) Synthesis, molecular structure, DFT studies and antimicrobial activities of some novel 3-(1-(3,4-dimethoxyphenethyl)-4,5-diphenyl-1H-imidazol-2-yl)-1H-indole derivatives and its molecular docking studies. J. of Molec. Stru., 1127 597-610.
30 Naureen S., Ijaz F., Munawar M. A., Asif N., Chaudhary F., Ashraf M, et al. (2017) Synthesis of tetrasubstituted imidazoles containing indole and their antiurease and antioxidant activities. J. of the Chil. Chem. Soci., 62(3) 3583-3587.
31 Mahmoodia, N. O., Nikokarb, I., Farhadia, M., & Ghavidasta, A. (2014) One-pot Multi-component Synthesis of Mono- and Bis-indolylimidazole Derivatives Using Zn2+@KSF and Their Antibacterial Activity. Zeitschrift für Naturforschung B, 69B(6) 715–720.
32 Nirwan, N., Pareek, C., & Swami, V. K. (2018) An Efficient Green Synthesis of Substituted Indolylimidazole Derivatives by Employing Reusable Catalyst under Microwave Irradiation. Indian J. of Hetero. Chem., 28(02) 249-54.
33 Nirwan, N., & Pareek, C. (2017) Synthesis of 2,4,5-trisubstituted imidazole and 4,5- disubstituted indolylimidazole derivatives by using Amberlyst A-15 as green, recyclable catalyst. Int. J. Sci. Res. Sci. and Tech., 8(3) 76-82.
34 Pareek, C., Pareek, D., Nirwan, N., & Jain, A. (2018) An Efficient Combinatorial Approach for Beta-Lactam Antibiotics with Novel Adjuvants against Gram-Negative Organisms to Combat Multi-Drug Resistance. Int. Acade. Con. Appl. Res. Eng. Sci. Tech., Brussels, Belgium. Diamond Scientific Publication: Lithuania, 134-43.
35 Benkli, K., Demirayak, S., Karaburun, N. G., Nuri, K., Iscan, G., & Ucucu, U. (2004) Synthesis and antimicrobial activities of some imidazole substituted indoles. Indian J. of Chem., 43B(1) 174-179.
36 Biradar, J. S., Sasidhar, B., Somappa, S. B., & Mugali, P. S. (2012) One-pot, solvent-free synthesis of 2,5-disubstituted indolylimidazoles by microwave irradiation. Der Pharm. Chem., 4(1) 437-41.
37 Nikoofar, K., & Dizgarani S. M. (2017) HNO3@nano SiO2: An efficient catalytic system for the synthesis of multi-substituted imidazoles under solvent-free conditions. J. of Saudi Chem. Soci., 21(7) 787-94.
38 Kelarev, V. I., Remezov, A. S., Karakhanov, R. A., Polivin, Y. N., et al. (1993) Vysshikh Uchebnykh Zavedenii. Kh. Khim. Tekhn. 35, 84-88. Chem Abstr., 1,186,915.
39 Molina, P., Fresneda, P. M., & Sanz M. A. (1998). Tetrahedron, 54, 9623-38.
40 Kobori, T., Hatanaka, Y., Ota, T., Nakanishi, M., et al. (1999). JP patent 11,199,582. Chem Abstr., 13,197,622.
41 Kobori T., Hatanaka Y., Ohjta T., Nakanishi M., et al. (1999). JP patent 11,199,583. Chem Abstr., 13,197,623.
42 Ota T., Nakanishi M., Tomisawa K., Kobori T., et al. (1999). Word patent WO 9,935,142. Chem Abstr., 13,173,652.
43 Ohta T., Nakanishi M., Tomizawa K., Kobori T., et al. (1999). JP patent 11,228,570. Chem Abstr., 131,170,350.
44 Ota T., Nakanishi M., Tomisawa K., Kobori T., et al. (1999). JP patent 11,228,572. Chem Abstr., 131,170,351.
45 Biradar J. S., Mugali P. S., Somappa S. B. and Rajesab P. (2008). Org. Chem. Indian J. 4, 408–11. Chem Abstr., 15,237,464.
46 Fresneda, P. M., Molina, P., & Sanz, M. A. (2001). Synlett, 218-21. Chem Abstr., 134,281,011.
47 Velsicol Chemical Corp. (1975). USA NL patent 7317578. Chem Abstr., 84,164,785.
48 Papaioannou C. G. (1972). US patent 3673208. Chem Abstr., 7,788,507.
49 Shaterian H. R., Ranjbar M., & Azizi K. (2011) Synthesis of highly substituted imidazoles using Bronsted acidic ionic liquid, Triphenyl(propyl-3-sulphonyl)phosphonium toluenesulfonate, as reusable catalyst. J. of the Iranian Chem. Soci., 8(4) 1120-1134.
1 Kawasaki I., Katsuma H., Nakayama Y., Yamashita M. Y., & Ohta S. (1998) Total Synthesis of Topsentin, Antiviral and Antitumor Bis(indolyl)imidazole. Heterocycles, 48 (9) 1887-1901.
2 Burres N. S., Barber D. A., Gunasekera S. P., Shen L.L., & Clement J. J. (1991) Antitumor activity and biochemical effects of Topsentin. Bio. Pharm., 42(4) 745-751.
3 Bartik K., Braekman J. C., Daloze D., Stoller C., Huysecom J., Vandevyver G., et al. (1987) Topsentins, new toxic bis-indole alkaloids from the marine sponge Tepsentiagenitrix. Canadian J. of Chem., 65(9) 2118–2121.
4 Morris S. A., & Andersen R. J. (1990) Brominated bis(indole) alkaloids from the marine sponge hexadella sp. Tetrahedron, 46(3) 715–720.
5 Sakemi S., & Sun H. H. (1991) Nortopsentins A, B, and C., Cytotoxic and antifungal imidazolediylbis[indoles] from the sponge Spongosoritesruetzleri. J. of Org. Chem., 56(13) 4304–4307.
6 Bao B., Sun Q., Xinsheng Y., Hong J., Lee C. O., Sim C. et al. (2005) Cytotoxic bisindole alkaloids from a marine sponge Spongosorites sp. J. of Nat. Prod., 68(5) 711–715.
7 Tsujii S., Rinehart K. L., Gunasekera S. P., Kashman Y., Cross S. S., Lui M. S., et al. ( 1988) Topsentin, bromotopsentin, and dihydrodeoxybromotopsentin: antiviral and antitumorbis(indolyl) imidazoles from Caribbean deep-sea sponges of the family Halichondriidae, Structural and synthetic studies. J. of Org. Chem., 53(23) 5446-5453.
8 Shin J., Seo Y., Cho K. W., Rho J. R., & Sim C. J. (1999) New bis(indole) alkaloids of the topsentin class from the sponge Spongosoritesgenitrix. J. of Nat. Prod., 62(4) 647– 649.
9 Casapullo A., Bifulco G., Bruno I. and Riccio R. (2000) New Bisindole Alkaloids of the Topsentin and Hamacanthin Classes from the Mediterranean Marine Sponge Rhaphisialacazei. J. of Nat. Prod., 63(4) 447–451.
10 McConnell O. J., Saucy. G., & Jacobs R. (1994). US Patent 5,290,777.
11 Wright A. E., Pomponi S. A., & Roberts J. A. (1999). Patent WO 9,942,092.
12 Sakemi, S., & Sun, H. H. (1991). Nortopsentins A, B, and C. Cytotoxic and antifungal imidazolediylbis [indoles] from the sponge Spongosorites ruetzleri. J. of Org. Chem., 56(13), 4304-4307.
13 Alvarado S., Roderts B. F., Wright A. E., & Chakrabarti D. (2013) The Bis(Indolyl)Imidazole Alkaloid Nortopsentin-A Exhibits Antiplasmodial Activity. Antimicrobial Ag. and Chemo., 57(5) 2362–2364.
14 Bewely C. A., & Faulkner D. J. (1998) Lithistid sponges: Star performers or hosts to the stars. Angewandte Chem. International Ed. in Eng., 37(16) 2162-2178.
15 Hogan I. T., & Sainsbury M. (1984) The synthesis of dendrodoine, 5-[3-(N,N-dimethylamino-1,2,4-thiadiazolyl]-3-indolylmethanone, a metabolite of the marine tunicate dendroda grossular. Tetrahedron, 40(4) 681-682.
16 Capon R. J., Peng C., & Dooms C. (2008) Trachycladindoles A-G: Cytotoxic heterocycles from an Australian marine sponge, Trachycladuslaevispirulifer. Org. & Biomo. Chem., 6(15) 2765-2771.
17 Hlasta D. J. (1991). US patent 5,017,584. Chem. Abstr., 115, 232,249.
18 Karabelas K., Lepisto M., & Sjo P. (2000). Word patent WO 2,000,078,750. Chem. Abstr., 13, 471,594.
19 Karabelas K., Lepisto M., & Sjo, P. (1999). Word patent WO 9,932,483. Chem. Abstr., 13, 158,823.
20 Levy, L. (1977) Proceedings, Soc. Exp. Biol. Med., 153 34-36. Chem. Abstr., 8,625,978.
21 Hoff, D. R. (1970). DE. 1,962,822. Chem. Abstr., 7,387,931.
22 Sato, H., Tsuda, M., Watanabe, K., & Kobayashi, J. (1998) Rhopaladins A-D, new indole alkaloids from marine tunicate Rhopalaea sp. Tetrahedron, 54(30) 8687-8690.
23 Doemling A., & Beck B. (2001). Word patent WO 2001,025,213. Chem. Abstr., 134,295,819.
24 Reddy Y. T., Konjeti R. S., Nidhish S., Reddy P. N., Freeman M. L., & Peter A. C. (2010) Novel substituted (Z)-5-((N-Benzyl-1H-indol-3-yl)methylene)imidazolidine-2,4-diones and 5-((N-Benzyl-1H-indol-3-yl)methylene)pyrimidine-2,4,6(1H,3H,5H)-triones as Potent Radio-sensitizing Agents. Bioorg. and Medi. Chem. Lett., 20(2) 600-602.
25 Roffey J. R. A. (1996) The Synthesis of Indole Containing Anticancer Compounds, PhD thesis, Loughborough University, UK.
26 Zoraghi R., Worrall L., See R. H., Strangman W., Popplewe W. L., Gong H., et al. (2011) MRSA Pyruvate Kinase as a Target for Bis-indole Alkaloids with Antibacterial Activities. J. of Bio. Chem., 286(52) 44716-44725.
27 Singh P., Kumar R., Tiwari S., Khanna R. S., Tewari A. K., Khanna H. D., et al. (2015) Docking, Synthesis and Evaluation of Antioxidant Activity of 2,4,5-Triaryl Imidazole. Clini. & Medi. Biochem., 1(1) 1-4.
28 Hilya V. P., Grishko L. G., Golubushina G. M., Arkhipova N. N. and Turov A. V. (1994) Khim. Geterotsikl. Soedin., 1063-1070. Chem., Abstr. 122,314,495.
29 Rajaramana D., Sundararajana G., Loganathb N. K., & Krishnasamya K. (2017) Synthesis, molecular structure, DFT studies and antimicrobial activities of some novel 3-(1-(3,4-dimethoxyphenethyl)-4,5-diphenyl-1H-imidazol-2-yl)-1H-indole derivatives and its molecular docking studies. J. of Molec. Stru., 1127 597-610.
30 Naureen S., Ijaz F., Munawar M. A., Asif N., Chaudhary F., Ashraf M, et al. (2017) Synthesis of tetrasubstituted imidazoles containing indole and their antiurease and antioxidant activities. J. of the Chil. Chem. Soci., 62(3) 3583-3587.
31 Mahmoodia, N. O., Nikokarb, I., Farhadia, M., & Ghavidasta, A. (2014) One-pot Multi-component Synthesis of Mono- and Bis-indolylimidazole Derivatives Using Zn2+@KSF and Their Antibacterial Activity. Zeitschrift für Naturforschung B, 69B(6) 715–720.
32 Nirwan, N., Pareek, C., & Swami, V. K. (2018) An Efficient Green Synthesis of Substituted Indolylimidazole Derivatives by Employing Reusable Catalyst under Microwave Irradiation. Indian J. of Hetero. Chem., 28(02) 249-54.
33 Nirwan, N., & Pareek, C. (2017) Synthesis of 2,4,5-trisubstituted imidazole and 4,5- disubstituted indolylimidazole derivatives by using Amberlyst A-15 as green, recyclable catalyst. Int. J. Sci. Res. Sci. and Tech., 8(3) 76-82.
34 Pareek, C., Pareek, D., Nirwan, N., & Jain, A. (2018) An Efficient Combinatorial Approach for Beta-Lactam Antibiotics with Novel Adjuvants against Gram-Negative Organisms to Combat Multi-Drug Resistance. Int. Acade. Con. Appl. Res. Eng. Sci. Tech., Brussels, Belgium. Diamond Scientific Publication: Lithuania, 134-43.
35 Benkli, K., Demirayak, S., Karaburun, N. G., Nuri, K., Iscan, G., & Ucucu, U. (2004) Synthesis and antimicrobial activities of some imidazole substituted indoles. Indian J. of Chem., 43B(1) 174-179.
36 Biradar, J. S., Sasidhar, B., Somappa, S. B., & Mugali, P. S. (2012) One-pot, solvent-free synthesis of 2,5-disubstituted indolylimidazoles by microwave irradiation. Der Pharm. Chem., 4(1) 437-41.
37 Nikoofar, K., & Dizgarani S. M. (2017) HNO3@nano SiO2: An efficient catalytic system for the synthesis of multi-substituted imidazoles under solvent-free conditions. J. of Saudi Chem. Soci., 21(7) 787-94.
38 Kelarev, V. I., Remezov, A. S., Karakhanov, R. A., Polivin, Y. N., et al. (1993) Vysshikh Uchebnykh Zavedenii. Kh. Khim. Tekhn. 35, 84-88. Chem Abstr., 1,186,915.
39 Molina, P., Fresneda, P. M., & Sanz M. A. (1998). Tetrahedron, 54, 9623-38.
40 Kobori, T., Hatanaka, Y., Ota, T., Nakanishi, M., et al. (1999). JP patent 11,199,582. Chem Abstr., 13,197,622.
41 Kobori T., Hatanaka Y., Ohjta T., Nakanishi M., et al. (1999). JP patent 11,199,583. Chem Abstr., 13,197,623.
42 Ota T., Nakanishi M., Tomisawa K., Kobori T., et al. (1999). Word patent WO 9,935,142. Chem Abstr., 13,173,652.
43 Ohta T., Nakanishi M., Tomizawa K., Kobori T., et al. (1999). JP patent 11,228,570. Chem Abstr., 131,170,350.
44 Ota T., Nakanishi M., Tomisawa K., Kobori T., et al. (1999). JP patent 11,228,572. Chem Abstr., 131,170,351.
45 Biradar J. S., Mugali P. S., Somappa S. B. and Rajesab P. (2008). Org. Chem. Indian J. 4, 408–11. Chem Abstr., 15,237,464.
46 Fresneda, P. M., Molina, P., & Sanz, M. A. (2001). Synlett, 218-21. Chem Abstr., 134,281,011.
47 Velsicol Chemical Corp. (1975). USA NL patent 7317578. Chem Abstr., 84,164,785.
48 Papaioannou C. G. (1972). US patent 3673208. Chem Abstr., 7,788,507.
49 Shaterian H. R., Ranjbar M., & Azizi K. (2011) Synthesis of highly substituted imidazoles using Bronsted acidic ionic liquid, Triphenyl(propyl-3-sulphonyl)phosphonium toluenesulfonate, as reusable catalyst. J. of the Iranian Chem. Soci., 8(4) 1120-1134.