146555-81-9Relevant articles and documents
Synthesis and antiproliferative evaluation of 7-aminosubstituted pyrroloiminoquinone derivatives
Beneteau, Valerie,Pierre, Alain,Pfeiffer, Bruno,Renard, Pierre,Besson, Thierry
, p. 2231 - 2234 (2000)
Coupling of five amines on the 7-methoxy-1,3,4,5-tetrahydropyrrolo[4,3,2-de]quinoline core was achieved and afforded, in particular, an opened analogue of the natural alkaloid wakayin. Evaluation of cytotoxic activity of compounds 2, 10-13 on L1210 cells afforded IC50 in the range 0.25-5.3 μM. (C) 2000 Elsevier Science Ltd.
Total synthesis of makaluvamine A/D, damirone B, batzelline C, makaluvone, and isobatzelline C featuring one-pot benzyne-mediated cyclization- functionalization
Oshiyama, Takashi,Satoh, Takahito,Okano, Kentaro,Tokuyama, Hidetoshi
, p. 9376 - 9383,8 (2020/08/20)
Total synthesis of pyrroloquinoline alkaloids, such as makaluvamine A/D, damirone B, batzelline C, makaluvone, and isobatzelline C, was achieved featuring a one-pot benzyne-mediated cyclization-functionalization reaction. The synthetic utility was demonstrated by the construction of the common pyrrolo[4,3,2-de]quinoline skeleton.
Synthesis of tetrahydropyrroloiminoquinone alkaloids based on electrochemically generated hypervalent iodine oxidative cyclization
Inoue, Keisuke,Ishikawa, Yuichi,Nishiyama, Shigeru
supporting information; experimental part, p. 436 - 439 (2010/04/24)
[Chemical equation presented] An approach to the synthesis of the tetrahydropyrroloiminoquinone alkaloids has been developed and applied to the preparation of N-1-βD-ribofuranosyltetrahydropyrroloiminoquinones. The strategy utilizes oxidative cyclization
Analogs of the marine alkaloid makaluvamines: Synthesis, topoisomerase II inhibition, and anticancer activity
Shinkre, Bidhan A.,Raisch, Kevin P.,Fan, Liming,Velu, Sadanandan E.
, p. 2890 - 2893 (2008/03/11)
Twelve analogs of makaluvamines have been synthesized. These compounds were evaluated for their ability to inhibit the enzyme topoisomerase II. Five compounds were shown to inhibit topoisomerase catalytic activity comparable to two known topoisomerase II
A biomimetic approach to the discorhabdin alkaloids: Total syntheses of discorhabdins C and E and dethiadiscorhabdin D
Aubart, Kelly Marshall,Heathcock, Clayton H.
, p. 16 - 22 (2007/10/03)
The characteristic spirodienone structure of the discorhabdin alkaloids is readily formed by reaction of the tyramine-substituted indoloquinonimines 26, 35, and 36 with cupric chloride, triethylamine, and oxygen. This cyclization provides a possibly biomimetic route to discorhabdins C and E (41 and 42). The unbrominated spirodienone 40 reacts with hydrogen over Pd/C to give enone 46. Bromination at the α position gives a mixture of bromoenones that undergo smooth conversion to dethiadiscorhabdin D (4) upon treatment with basic alumina.
New synthetic approach to pyrroloiminoquinone marine alkaloids. Total synthesis of makaluvamines A, D, I, and K
Iwao, Masatomo,Motoi, Osamu,Fukuda, Tsutomu,Ishibashi, Fumito
, p. 8999 - 9010 (2007/10/03)
A new entry into pyrroloiminoquinone marine alkaloids, makaluvamines, has been developed. The key 1,3,4,5-tetrahydropyrrolo[4,3,2-de]quinoline intermediates 11 and 18 were prepared by aryne-mediated cyclization of the 4- chloro-6-methoxytryptamine derivatives 10 and 17, respectively. The requisite substituents at the indole 4- and 3-positions of 10 and 17 were efficiently assembled by sequential use of directed lithiation of 1-triisopropylsilyl-6- methoxygramine (6) and fluoride ion-induced elimination-addition of the methiodide of 4-chloro-l-triisopropylsilyl-6-methoxygramine (7) as key reactions.
Synthesis of pyrrolo[4,3,2-de]quinolines from 6,7-dimethoxy-4-methylquinoline. Formal total syntheses of damirones A and B, batzelline C, isobatzelline C, discorhabdin C, and makaluvamines A-D
Roberts, David,Joule, John A.,Antonieta Bros,Alvarez, Mercedes
, p. 568 - 577 (2007/10/03)
2-Amino-4-nitrophenol and 2-methoxy-5-nitroaniline were converted into the 5-nitroquinolines 6b and 6d, respectively, and then the latter into nitro-acetal 6f. 6,7-Dimethoxy-4-methylquinoline (6g) was nitrated at C-5 and then the methyl substituent conver
Efficient syntheses of the marine alkaloids makaluvamine D and discorhabdin C: The 4,6,7-trimethoxyindole approach
Sadanandan,Pillai,Lakshmikantham,Billimoria,Culpepper,Cava
, p. 1800 - 1805 (2007/10/02)
A new and efficient synthesis of the tricyclic quinonimine 20 as its trifluoroacetate 23 has been developed starting from the commercially available 2,4,5-trimethoxybenzaldehyde and proceeding via the hitherto unknown 4,6,7-trimethoxyindole (7). Quinonimi
Total syntheses of makaluvamines A, B, C, D and E, cytotoxic pyrroloiminoquinone alkaloids isolated from marine sponge bearing inhibitory activities against topoisomerase II
Izawa, Takao,Nishiyama, Shigeru,Yamamura, Shosuke
, p. 13593 - 13600 (2007/10/02)
Syntheses of makaluvamines A, B, C, D and E (1-5), new members of tetrahydropyrroloiminoquinone alkaloids, have been successfully carried out. Particularly, olefin introduction for makaluvamines B and E could be achieved by Pd-mediated and E2 t
Synthetic studies of the pyrroloquinoline nucleus of the makaluvamine alkaloids. Synthesis of the topoisomerase II inhibitor makaluvamine D
White, James D.,Yager, Kraig M.,Yakura, Takayuki
, p. 1831 - 1838 (2007/10/02)
A new synthesis of the pyrrolo[4,3,2-de]quinoline system characteristic of a class of marine alkaloids which includes the prianosins, discorhabdins, and other antineoplastic agents has been developed. The approach is exemplified in a total synthesis of ma
