478916-44-8Relevant articles and documents
The antimicrobial natural product chuangxinmycin and some synthetic analogues are potent and selective inhibitors of bacterial tryptophanyl tRNA synthetase
Brown, Murray J.,Carter, Paul S.,Fenwick, Ashley E.,Fosberry, Andrew P.,Hamprecht, Dieter W.,Hibbs, Martin J.,Jarvest, Richard L.,Mensah, Lucy,Milner, Peter H.,O'Hanlon, Peter J.,Pope, Andrew J.,Richardson, Christine M.,West, Andrew,Witty, David R.
, p. 3171 - 3174 (2002)
The antimicrobial natural product chuangxinmycin has been found to be a potent and selective inhibitor of bacterial tryptophanyl tRNA synthetase (WRS). A number of analogues have been synthesised. The interaction with WRS appears to be highly constrained, as only sterically smaller analogues afforded significant inhibition. The only analogue to show inhibition comparable to chuangxinmycin also had antibacterial activity. WRS inhibition may contribute to the antibacterial action of chuangxinmycin.
New total synthesis of (±)-chuangxinmycin
Kato, Keisuke,Ono, Machiko,Akita, Hiroyuki
, p. 1805 - 1808 (2007/10/03)
(±)-4'-Iodoindolmycenate 6 was stereoselectively converted into the (±)-(2,3)-syn-2-thioacetoxy ester 16 with retention of C2-stereochemistry in (±)-6. Palladium-catalysed cyclisation of indolyl iodide and the internal C2 thiol group of the substrate (±)-17 derived from (±)-16 gave the (±)-cis methyl ester 2 of natural chuangxinmycin (1).
A new, general entry to 4-substituted indoles. Synthesis of (S)-(-)-pindolol and (±)-chuangxinmycin
Ishibashi, Hiroyuki,Tabata, Takashi,Hanaoka, Kyoko,Iriyama, Hiroko,Akamatsu, Susumu,Ikeda, Masazumi
, p. 489 - 492 (2007/10/02)
A new method for synthesis of 4-substituted indoles has been developed by using the 7-arylthio-6-7-dihydroindol-4(5H) one 5 as a common intermediate. The method was applied to the synthesis of (S)-(-)-pindolol (11) and (±)-chuangxinmycin (16).
