63339-68-4Relevant academic research and scientific papers
New total synthesis of (-)- and (+)-chuangxinmycins
Kato, Keisuke,Ono, Machiko,Akita, Hiroyuki
, p. 2295 - 2298 (1997)
Stereoselective total syntheses of (-)-(4S,5R)- and (+)-(4R,5S)-chuangxinmycins 1 were achieved based on the enzymatic syntheses of (2R,3S)- and (2S,3R)-epoxy butanoates 8, respectively. Chiral intermediates such as (2R,3S)- and (2S,3R)-2-hydroxy-3-(4'-iodoindol-3'-yl)butanoate 5 for the chiral synthesis of (-)- and (+)-1 were also obtained by the enantioselective hydrolysis of the corresponding acetate 6 by lipase.
Indole derivatives and its preparation method
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, (2018/02/04)
The invention relates to a novel antibacterial compound, i.e. an indole derivative, a three-dimensional isomerism or medical salt, solvent compound or aquo-complex as well as a preparation method, a medicine composition containing the compound and an application of the compound in preparing an antibiotic drug.
Nickel-mediated inter- and intramolecular C-S coupling of thiols and thioacetates with aryl iodides at room temperature
Xu, Xiao-Bo,Liu, Jian,Zhang, Jian-Jian,Wang, Ya-Wen,Peng, Yu
, p. 550 - 553 (2013/04/11)
A Ni(0)-catalyzed intermolecular cross-coupling of various functionalized thiols and aryl iodides has been developed and successfully extended to less explored intramolecular versions, where thioacetates could also be utilized as the strategic surrogate. Air-stable precatalysts, very mild conditions, and an easy protocol allow rapid access to medicinally useful aryl thioethers, as demonstrated in the facile synthesis of (±)-chuangxinmycin as a key step.
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 (2007/10/03)
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 (±)-, (-)- and (+)-chuangxinmycins
Kato, Keisuke,Ono, Machiko,Akita, Hiroyuki
, p. 10055 - 10062 (2007/10/03)
(±)-2-Hydroxy-3-(1H-4′-iodoindol-3′-yl)butanoate 6 was stereoselectively converted into the (±)-(2,3)-syn-2-thioacetoxy ester 13 with retention of C2-stereochemistry in (±)-6. Palladium-catalyzed cyclization of indolyl iodide and the internal C2 thiol group of the substrate (±)-14 gave the (±)-cis methyl ester 2 of natural chuangxinmycin (1). Stereoselective total syntheses of (-)-(4S,5R)- and (+)-(4R,5S)-chuangxinmycins 1 were achieved based on the enzymatic syntheses of (2R,3S)- and (2S,3R)-epoxy butanoates 9, respectively. Chiral intermediates such as (2R,3S)- and (2S,3R)-2-hydroxy-3-(1H-4′-iodoindol-3′-yl)butanoate 6 for the chiral synthesis of (-)- and (+)-1 were also obtained by the enantioselective hydrolysis of the corresponding acetate (±)-16 by lipase.
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).
New, concise route to indoles bearing oxygen or sulfur substituent at the 4-position. Synthesis of (±)- and (S)-(-)-pindolol and (±)-chuangxinmycin
Ishibashi,Akamatsu,Iriyama,Hanaoka,Tabata,Ikeda
, p. 271 - 276 (2007/10/02)
A new method for the synthesis of 4-alkoxy- and 4-[alkyl (or aryl)thio]indoles has been developed by using the indolone 3 as a common intermediate. The indolone 3 was prepared from N-(phenylsulfonyl)pyrrole (7) and the α-chlorosulfide 8 in four steps. Heating of a mixture of 3 and an appropriate alcohol in the presence of p-toluenesulfonic acid and cupric chloride afforded the 4-alkoxyindoles 11a-d. The method was applied to the synthesis of (±)-pindolol (19) and (S)-(-)-pindolol (20). Thiols also reacted with 3 in the presence of boron trifluoride to give 4-[aryl (or alkyl)thio]indoles 12, 21a, b, and 22a-d. The (indol-4-ylthio)acetate 22c was employed as a key intermediate for a concise total synthesis of (±)- chuangxinmycin (27).
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).
Synthetic Studies in the Indole Series. Preparation of the Unique Antibiotic Alkaloid Chuangxinmycin by a Nitro Group Displacement Reaction
Kozikowski, Alan P.,Greco, Michael N.,Springer, James P.
, p. 7622 - 7626 (2007/10/02)
The total synthesis of the unique sulfur-containing antibiotic indole alkaloid chuangxinmycin is described.This compound, first isolated by Chinese chemists at the Institute of Materia Medica, was assembled from 2,6-dinitrotoluene by a scheme that combine
