A novel approach to the indoloquinoline alkaloids cryptotackieine and cryptosanguinolentine by application of cyclization of o-vinylsubstituted arylheterocumulenes

被引:73
作者
Fresneda, PM [1 ]
Molina, P [1 ]
Delgado, S [1 ]
机构
[1] Univ Murcia, Fac Quim, Dept Quim Organ, E-30071 Murcia, Spain
关键词
alkaloids; aza-Wittig reaction; microwave heating; insertion reaction; nitrogen heterocycles;
D O I
10.1016/S0040-4020(01)00597-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
1-Methyl-3-(o-azidophenyl)quinoline-2-one prepared by cyclization of the corresponding o-vinylsubstituted isocyanate under microwave irradiation is directly converted into cryptotackieine 1 by an intramolecular aza-Wittig reaction with trimethylphosphine; alternatively heating followed by reduction of the resulting indoloquinoline derivative provided cryptosanguinolentine 2. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:6197 / 6202
页数:6
相关论文
共 37 条
[1]   Probing the N-5 region of the indoloquinoline alkaloid, cryptolepine for anticryptococcal activity [J].
Ablordeppey, SY ;
Fan, PC ;
Clark, AM ;
Nimrod, A .
BIOORGANIC & MEDICINAL CHEMISTRY, 1999, 7 (02) :343-349
[2]   Formal total synthesis of the alkaloid cryptotackieine (neocryptolepine) [J].
Alajarin, M ;
Molina, P ;
Vidal, A .
JOURNAL OF NATURAL PRODUCTS, 1997, 60 (07) :747-748
[3]  
[Anonymous], 1983, P 1 INT SEMINAR CRYP
[4]   1H-INDAZOLE AND 2H-INDAZOLE BY THERMAL AND PHOTOLYTIC DECOMPOSITION OF ORTHO-AZIDOBENZOIC ACID AND ORTHO-AZIDOBENZALDEHYDE DERIVATIVES [J].
ARDAKANI, MA ;
SMALLEY, RK ;
SMITH, RH .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1983, (10) :2501-2506
[5]   New synthesis of benzo-δ-carbolines, cryptolepines, and their salts:: In vitro cytotoxic, antiplasmodial, and antitrypanosomal activities of δ-caribolines, benzo-δ-carbolines, and cryptolepines [J].
Arzel, E ;
Rocca, P ;
Grellier, P ;
Labaeïd, M ;
Frappier, F ;
Guéritte, F ;
Gaspard, C ;
Marsais, F ;
Godard, A ;
Quéguiner, G .
JOURNAL OF MEDICINAL CHEMISTRY, 2001, 44 (06) :949-960
[6]   Ethnobotanical-directed discovery of the antihyperglycemic properties of cryptolepine:: Its isolation from Cryptolepis sanguinolenta, synthesis, and in vitro and in vivo activities [J].
Bierer, DE ;
Fort, DM ;
Mendez, CD ;
Luo, J ;
Imbach, PA ;
Dubenko, LG ;
Jolad, SD ;
Gerber, RE ;
Litvak, J ;
Lu, Q ;
Zhang, PS ;
Reed, MJ ;
Waldeck, N ;
Bruening, RC ;
Noamesi, BK ;
Hector, RF ;
Carlson, TJ ;
King, SR .
JOURNAL OF MEDICINAL CHEMISTRY, 1998, 41 (06) :894-901
[7]   In vitro and in vivo antiplasmodial activity of cryptolepine and related alkaloids from Cryptolepis sanguinolenta [J].
Cimanga, K ;
DeBruyne, T ;
Pieters, L ;
Vlietinck, AJ .
JOURNAL OF NATURAL PRODUCTS, 1997, 60 (07) :688-691
[8]   Antibacterial and antifungal activities of neocryptolepine, biscryptolepine and cryptoquindoline, alkaloids isolated from Cryptolepis sanguinolenta [J].
Cimanga, K ;
De Bruyne, T ;
Pieters, L ;
Totte, J ;
Tona, L ;
Kambu, K ;
Vanden Berghe, D ;
Vlietinck, AJ .
PHYTOMEDICINE, 1998, 5 (03) :209-214
[9]   In vitro biological activities of alkaloids from Cryptolepis sanguinolenta [J].
Cimanga, K ;
DeBruyne, T ;
Lasure, A ;
VanPoel, B ;
Pieters, L ;
Claeys, M ;
VandenBerghe, D ;
Kambu, K ;
Tona, L ;
Vlietinck, AJ .
PLANTA MEDICA, 1996, 62 (01) :22-27
[10]   ELUCIDATION OF THE STRUCTURE OF QUINDOLINONE, A MINOR ALKALOID OF CRYPTOLEPIS-SANGUINOLENTA - SUBMILLIGRAM H-1-C-13 AND H-1-N-15 HETERONUCLEAR SHIFT CORRELATION EXPERIMENTS USING MICRO INVERSE-DETECTION [J].
CROUCH, RC ;
DAVIS, AO ;
SPITZER, TD ;
MARTIN, GE ;
SHARAF, MMH ;
SCHIFF, PL ;
PHOEBE, CH ;
TACKIE, AN .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1995, 32 (03) :1077-1080