The ß-carboline alkaloids possess a wide diversity of important biochemical effects and pharmacological properties. A series of ß-carboline derivatives were synthesized from L-tryptophan through the Pictet-Spengler reaction and oxidation of K2Cr2O7 via sequential one-pot synthesis method. In vitro anti-bacterial, insecticidal, and cytotoxic activities of all synthesized compounds were investigated by the tablet diffusion, leaf disc, and MTT methods, respectively. Some of the compounds(1a, 1b, 1c and 1j) exhibited obvious anti-bacterial effects and some (1-3) had significant cytotoxic activities against tumor cells 3LL, MCF-7, BGC-823 and QGY-7701, with IC50 values of 7.79, 5.75, 3.53 and 4.02 µg/mL, respectively. No insecticidal activity against third stage instar larvae of Mythimnaseparata Walker were observed under the tested concentration.
Cite this article:
Avneesh Awasthy, Om Prakash Agrawal. Synthesis and Antimicrobial and Anticancer Activity of β-Carboline Analogues. Research Journal of Pharmacy and Technology. 2022; 15(9):3969-4. doi: 10.52711/0974-360X.2022.00665
Avneesh Awasthy, Om Prakash Agrawal. Synthesis and Antimicrobial and Anticancer Activity of β-Carboline Analogues. Research Journal of Pharmacy and Technology. 2022; 15(9):3969-4. doi: 10.52711/0974-360X.2022.00665 Available on: https://www.rjptonline.org/AbstractView.aspx?PID=2022-15-9-25
1. Zhou TS, Ye WC, Wang ZT. (1998) β-Carboline alkaloids from Hypodemabiumaquamuloso-pilosum. Phytochemistry, 49,1807-1809.
2. AliveluSamala, Srinivasa Murthy M, Krishna Mohan Gottumukkala. A Comprehensive Review on Recent Advances in Synthesis and Pharmacotherapeutic Potential of Betacarbolines. Research J. Pharm. and Tech 2018; 11(8): 3547-3560. doi: 10.5958/0974-360X.2018.00655.8.
3. Vikram Singh, N.K. Kaushik, Ram Singh. Metallosulpha Drugs: Synthesis and Bioactivity. Asian J. Research Chem. 4(3): March 2011; Page 339-347
4. Carbrera GM, Seldes AM. (1999) A beta-carboline alkaloid from the soft coral Lignopsisspongiosum, Journal of NaturalProducts, 62, 759-760.
5. Kotanen S, Huybrechts J, Cerstiaens A. (2003) Identification of tryptophan and beta-carboline as paralysins in larvae of the yellowmealworm, Tenebriomolitor. Biochemical and Biophysical Research Communications, 310, 64-71.
6. Beck O, Lundman A. (1983) Occurrence of 6-hydroxy-1-methyl-1, 2, 3, 4-tetrahydro-β-carboline in tissues and body fluids of rat,Biochemical Pharmacology, 32, 1507-1510.
7. Lippke KP, Schunack WG, Wolfgang W, Mueller WE. (1983) Beta-carbolines as benzodiazepine receptor ligands. 1. Synthesis andbenzodiazepine receptor interaction of esters of beta-carboline-3-carboxylic acid. Journal of Medicinal Chemistry, 26, 499-503.
8. Csányi D, Hajós G, Riedl Z, (2000) Synthesis of two new heteroaromatic β-carboline-fused pentacycles. Observation of a newintercalating agent. Bioorganic and Medicinal Chemistry Letters, 10, 1767-1769.
9. Song YC, Wang J, Teng SF, Kesuma D. (2002) β-Carbolines as specific inhibitors of cyclin-dependent kinases. Bioorganic and Medicinal Chemistry Letters, 12, 1129-1132.
10. Deveau AM, Labroli MA, Dieckhaus CM. (2001) The synthesis of amino-acid functionalized β-carbolinesastopoisomerase IIinhibitors. Bioorganic and Medicinal Chemistry Letters, 11, 125-1255.
11. Yao WQ, Wang JR, Zhang PZ. (2004) Effects of Peganumharmala extract on the growth and antioxidase activity of wheatseedlings. ActaBotanicaBoreali-OccidentaliaSinica, 24, 1096-1099.
12. Weng QF, Zhong GH, Hu MY. (2005) Bioactivities and physiological effects of extracts of Peganumharmala againstBursaphelenchusxylophilus. ScientiaAgriculturaSinica, 38, 2014-2022.
13. Zhao XM, Zen ZH. (2005) The research of the pesticidal activity on diffident Peganumharmala extractions. Chinese Agricultural Science Bulletin, 21, 278-279.
14. Rharrabe K, Bakrim A, Ghailani N, Sayah F. (2007) Bioinsecticidal effect of harmaline on Plodiainterpunctella development(Lepidoptera: Pyralidae). Pesticide Biochemistry and Physiology, 89, 137–145
15. Snyder HR, Parmerter SM, Katz L. (1948) The synthesis of derivatives of β-carboline. III. The nitration of Harman. Journal of theAmerican Chemical Society, 70, 222–225.
16. Snyder HR, Werber FX. (1950) Polyphosphoric acid as a dehydrating agent. I. The cyclodehydration of some α-acylamino-β-arylpropionic acids. Journal of the American Chemical Society, 72, 2962-2965.
17. Clemo GR, Holt RJW. (1953) Synthesis of 5, 6, 7, 8-tetrahydro-1-methyl-β-carboline. Journal of the Chemical Society, 1313-1314.
18. Bamgbose SOA, Dramane KL, Okogun, JI. (1977) Synthesis and preliminary pharmacological studies of 1-ethyl-β -carboline.PlantaMedica, 31, 193-200.
19. Ivanov I, Nikolova S, Statkova-Abeghe S. (2005) A simple method for the synthesis of 1-substituted β-carboline derivatives fromtryptamine and carboxylic acids in polyphosphoric acid. Heterocycles, 65, 2483-2492.
20. Prinsep MR, Blunt JW, Munro M HG. (1991) New cytotoxic β-carboline alkaloids from the marine bryozoan, Cribricellinacribraria. Journal of Natural Products, 54, 1068-1076.
21. Kulkarni A, Abid M, Torok B, Huang X. (2009) A direct synthesis of β-carbolines via a three-step one-pot domino approach with abifunctionalPd/C/K-10 catalyst. Tetrahedron Letters, 50, 1791-1794.
22. Song Y, Wang J, Teng SF, Kesuma D, Deng Y, Duan J, Wang JH, Qi R, Sim MM. (2002) β-Carbolines as specific inhibitors ofcyclin-dependent kinases. Bioorganic and Medicinal Chemistry Letters, 12, 1129-1132.
23. Pal B, Jaisankar P, Giri VS. (2003) Microwave assisted Pictet-Spengler and Bischler-Napieralski reactions. Synthetic Communications, 33, 2339-2348.
24. Inoue S, Tokuyama T, Takai K. (1983) Picomole analyses of tryptophan by derivatization to 9-hydroxymethyl-beta-carboline. Analytical Biochemistry, 132, 468-80
25. Wu WJ, Tu YQ, Zhu JB. (1992) CelangulinⅡ,Ⅲ and IV: New Insecticidal sesquiterpenoids from Celastrus. Journal of Natural Products, 55, 1294-1296.
26. Zheng YT, Zhang WF, Ben KL, Wang JH. (1995) In vitro immunotoxicity and cytotoxicity of trichosanthin against human normalimmunocytes and lekeumia-lymphoma cells. Immunopharmacology and Immunotoxicology, 17, 69-79.