Synthesis and bioactivity of β-carboline derivatives

Natural Product Communications

Volumn 5, Issue 10, 2010, Pages 1591-1596

  Li, Shengkun ^a   Yang, Bing ^a   Zhang, Qianliang ^a   Zhang, Jiwen ^a,b   Wang, Junru ^a   Wu, Wenjun ^a  

^a NORTHWEST A F UNIVERSITY   (China)

^b Talimu University   (China)

Author keywords

Bioactivity; Pictet reaction; carboline alkaloids

Indexed keywords

(9H PYRIDO[3,4 B]INDOL 9 YL)METHANOL; 1 (2 NITROPHENYL) 9H PYRIDO[3,4 B]INDOLE; 1 (3 NITROPHENYL) 9H PYRIDO[3,4 B]INDOLE; 1 (4 METHOXYPHENYL) 9H PYRIDO[3,4 B]INDOLE; 1 ETHYL 9H PYRIDO[3,4 B]INDOLE; 1 ISOPROPYL 9H PYRIDO[3,4 B]INDOLE; 1 METHYLTRYPTOLINE; 1 PHENYL 9H PYRIDO[3,4 B]INDOLE; 1 PROPYL 9H PYRIDO[3,4 B]INDOLE; 2 (9H PYRIDO[3,4 B]INDOL 1 YL)PHENOL; 2 METHOXY 4 (9H PYRIDO [3,4 B]INDOL 1 YL)PHENOL; BETA CARBOLINE DERIVATIVE; METHANOL; STREPTOMYCIN; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ARTICLE; CANCER CELL CULTURE; CYTOTOXICITY; DRUG SYNTHESIS; GRAM NEGATIVE BACTERIUM; GRAM POSITIVE BACTERIUM; IC 50; INSECTICIDAL ACTIVITY; LARVAL STAGE; MOTH; MYTHIMNA SEPARATA; ONE POT SYNTHESIS; PICTET SPENGLER REACTION;

BACTERIA (MICROORGANISMS); MYTHIMNA SEPARATA;

EID: 77957904609     PISSN: 1934578X     EISSN: 15559475     Source Type: Journal    
DOI: 10.1177/1934578x1000501016     Document Type: Article

References (24)

1. Zhou TS, Ye WC, Wang ZT. (1998) β-Carboline alkaloids from Hypodemabium aquamuloso-pilosum. Phytochemistry, 49, 1807-1809
2. Carbrera GM, Seldes AM. (1999) A beta-carboline alkaloid from the soft coral Lignopsis spongiosum, Journal of Natural Products, 62, 759-760.
3. Kotanen S, Huybrechts J, Cerstiaens A. ( 2003) Identification of tryptophan and beta-carboline as paralysins in larvae of the yellow mealworm, Tenebrio molitor. Biochemical and Biophysical Research Communications, 310, 64-71. (Pubitemid 37162763)
4. 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. (Pubitemid 13096009)
5. Lippke KP, Schunack WG, Wolfgang W, Mueller WE. (1983) Beta-carbolines as benzodiazepine receptor ligands. 1. Synthesis and benzodiazepine receptor interaction of esters of beta-carboline-3-carboxylic acid. Journal of Medicinal Chemistry, 26, 499-503.
6. Csányi D, Hajós G, Riedl Z, (2000) Synthesis of two new heteroaromatic β-carboline-fused pentacycles. Observation of a new intercalating agent. Bioorganic & Medicinal Chemistry Letters, 10, 1767-1769. (Pubitemid 30495259)
7. Song YC, Wang J, Teng SF, Kesuma D. (2002) β-Carbolines as specific inhibitors of cyclin-dependent kinases. Bioorganic & Medicinal Chemistry Letters, 12, 1129-1132. (Pubitemid 34242818)
8. Deveau AM, Labroli MA, Dieckhaus CM. (2001) The synthesis of amino-acid functionalized β-carbolines astopoisomerase II inhibitors. Bioorganic & Medicinal Chemistry Letters, 11, 125-1255.
9. Yao WQ, Wang JR, Zhang PZ. (2004) Effects of Peganum harmala extract on the growth and antioxidase activity of wheat seedlings. Acta Botanica Boreali-Occidentalia Sinica, 24, 1096-1099.
10. Weng QF, Zhong GH, Hu MY. (2005) Bioactivities and physiological effects of extracts of Peganum harmala against Bursaphelenchus xylophilus. Scientia Agricultura Sinica, 38, 2014-2022.
11. Zhao XM, Zen ZH. (2005) The research of the pesticidal activity on diffient Peganum harmala extractions. Chinese Agricultural Science Bulletin, 21, 278-279.
12. Rharrabe K, Bakrim A, Ghailani N, Sayah F. (2007) Bioinsecticidal effect of harmaline on Plodia interpunctella development (Lepidoptera: Pyralidae). Pesticide Biochemistry and Physiology, 89, 137-145 (Pubitemid 47313514)
13. Snyder HR, Parmerter SM, Katz L. (1948) The synthesis of derivatives of β-carboline. III. The nitration of Harman. Journal of the American Chemical Society, 70, 222-225.
14. 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.
15. Clemo GR, Holt RJW. (1953) Synthesis of 5,6,7,8-tetrahydro-1-methyl- β-carboline. Journal of the Chemical Society, 1313-1314.
16. Bamgbose SOA, Dramane KL, Okogun, JI. (1977) Synthesis and preliminary pharmacological studies of 1-ethyl-β -carboline. Planta Medica, 31, 193-200.
17. Ivanov I, Nikolova S, Statkova-Abeghe S. (2005) A simple method for the synthesis of 1-substituted β-carboline derivatives from tryptamine and carboxylic acids in polyphosphoric acid. Heterocycles, 65, 2483-2492.
18. Prinsep MR, Blunt JW, Munro M HG. (1991) New cytotoxic β-carboline alkaloids from the marine bryozoan, Cribricellina cribraria. Journal of Natural Products, 54, 1068-1076.
19. Kulkarni A, Abid M, Torok B, Huang X. (2009) A direct synthesis of β-carbolines via a three-step one-pot domino approach with a bifunctional Pd/C/K-10 catalyst. Tetrahedron Letters, 50, 1791-1794.
20. Song Y, Wang J, Teng SF, Kesuma D, Deng Y, Duan J, Wang JH, Qi R, Sim MM. (2002) β-Carbolines as specific inhibitors of cyclin-dependent kinases. Bioorganic & Medicinal Chemistry Letters, 12, 1129-1132. (Pubitemid 34242818)
21. Pal B, Jaisankar P, Giri VS. (2003) Microwave assisted Pictet-Spengler and Bischler-Napieralski reactions. Synthetic Communications, 33, 2339-2348. (Pubitemid 36818840)
22. Inoue S, Tokuyama T, Takai K. (1983) Picomole analyses of tryptophan by derivatization to 9-hydroxymethyl-beta-carboline. Analytical Biochemistry, 132, 468-80
23. Wu WJ, Tu YQ, Zhu JB. (1992) Celangulin II,III and IV: New Insecticidal sesquiterpenoids from Celastrus. Journal of Natural Products, 55, 1294-1296.
24. Zheng YT, Zhang WF, Ben KL, Wang JH. (1995) In vitro immunotoxicity and cytotoxicity of trichosanthin against human normal immunocytes and lekeumia-lymphoma cells. Immunopharmacology and Immunotoxicology, 17, 69-79.