1158951-70-2Relevant academic research and scientific papers
IMPROVED SYNTHESIS OF CAPURAMYCIN AND ITS ANALOGUES
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Page/Page column 37, (2015/03/13)
Provided herein are compounds of Formula I, Formula II, and Formula X, which are useful for the treatment of infectious diseases. Also provided herein are processes for preparing 1-[5-0-[4,6-Dideoxy-6-oxo-6-[[[(3S)-hexahydro-2-oxo-1H-azepine]-3-y1]amino]-Pβ-L-erythro-4- hexenopyranosyl]-3-0-methyl 6-deoxy-6-amino-α-L-talofuranuronosyl]-1,2,3,4-tetrahydro-2,4- dioxopyrimidine (capuramycin), analogues thereof, and intermediates useful therefore. Also provided herein are III, IIIa, and IX, which are useful in the process for preparing capuramycin and/or a certain compound of Formula I.
Improved synthesis of capuramycin and its analogues
Wang, Yong,Siricilla, Shajila,Aleiwi, Bilal A.,Kurosu, Michio
, p. 13847 - 13858 (2013/10/22)
Capuramycin and its congeners are considered to be important lead molecules for the development of a new drug for multidrug-resistant (MDR) Mycobacterium tuberculosis infections. Extensive structure-activity relationship studies of capuramycin to improve the efficacy have been limited because of difficulties in selectively chemically modifying the desired position(s) of the natural product with biologically interesting functional groups. We have developed efficient syntheses of capuramycin and its analogues by using new protecting groups, derived from the chiral (chloro-4-methoxyphenyl)(chlorophenyl)methanols, for the uridine ureido nitrogen and primary alcohol. The chiral nonracemic (2,6-dichloro-4-methoxyphenyl)(2,4-dichlorophenyl)methanol derivative is a useful reagent to resolve rac-3-amino-1,3-dihydro-5-phenyl-2H-1,4-benzodiazepin- 2-one, the (S)-configuration isomer of which plays a significant role in improving the mycobactericidal activity of capuramycin. Battling TB: Capuramycin and its congeners (see scheme) are considered to be important lead molecules for the development of a new drug for multidrug-resistant Mycobacterium tuberculosis infections. Efficient synthesis of capuramycin and its analogues by using new protecting groups for the uridine ureido nitrogen and primary alcohol was accomplished. Copyright
Concise synthesis of capuramycin
Kurosu, Michio,Li, Kai,Crick, Dean C.
supporting information; experimental part, p. 2393 - 2396 (2009/10/23)
A concise total synthesis of capuramycin (1), a promising preclinical TB drug lead, is achieved by high-yield formations of the cyanohydrin 5a and 4″,5″-glycal derivative 12. Capuramycin can be synthesized in eight steps from the uridine building block 5a with 30% overall yield. The synthetic intermediates reported here are useful for generation of analogs to improve pharmacokinetic properties of capuramycin.
