73341-72-7

Usage

Uses

Macbecin I is an ansamycin antibiotic inhibitor of Hsp90 activity.

Biological Activity

Ansamycin antibiotic compound that inhibits Hsp90 activity (IC 50 = 2 μ M) by binding to the ATP-binding site. Exhibits antitumor and cytocidal activities (IC 50 ~ 0.4 μ M) by causing degradation of key oncogenic client proteins such as ErbB2 and cRaf1. Displays higher affinity and potency than geldanamycin (9,13-Dihydroxy-8,14,19-trimethoxy-4,10,12,16-tetramethyl-2-azabicyclo[16.3.1]docosa-4,6,10,18,21-pentaene-3,20,22-trione, 9-carbamate ).

InChI:InChI=1/C30H42N2O8/c1-16-10-9-11-17(2)29(35)32-23-15-21(33)14-22(25(23)34)27(38-7)20(5)13-24(37-6)28(39-8)19(4)12-18(3)26(16)40-30(31)36/h9-12,14-16,19-20,24,26-28H,13H2,1-8H3,(H2,31,36)(H,32,35)/b10-9+,17-11-,18-12+

Upstream product

• 128854-42-2 (E)-(2S,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-5-iodo-2,4-dimethyl-pent-4-enoic acid 
• 170707-65-0 (2E,4Z,8E)-(6S,7R,10S,11R,12S,14S,15R)-15-(2,5-Dimethoxy-3-nitro-phenyl)-11,12,15-trimethoxy-7-(4-methoxy-benzyloxy)-2,6,8,10,14-pentamethyl-pentadeca-2,4,8-trienoic acid ethyl ester 
• 170707-60-5 2,5-Dimethoxy-1-nitro-3-[(7E,11E)-(1R,2S,4S,5R,6S,9R,10S)-1,4,5,14-tetramethoxy-9-(4-methoxy-benzyloxy)-2,6,8,10-tetramethyl-tetradeca-7,11-dienyl]-benzene 
• 170707-62-7 (2Z,6E)-(4S,5R,8S,9R,10S,12S,13R)-13-(2,5-Dimethoxy-3-nitro-phenyl)-9,10,13-trimethoxy-5-(4-methoxy-benzyloxy)-4,6,8,12-tetramethyl-trideca-2,6-dienoic acid methyl ester 
• 170707-66-1 (2E,4Z,8E)-(6S,7R,10S,11R,12S,14S,15R)-15-(3-Amino-2,5-dimethoxy-phenyl)-11,12,15-trimethoxy-7-(4-methoxy-benzyloxy)-2,6,8,10,14-pentamethyl-pentadeca-2,4,8-trienoic acid ethyl ester 
• 206661-17-8 (2Z,6E)-(4S,5R,8S,9R,10S,12S,13R)-13-(2,5-Dimethoxy-3-nitro-phenyl)-9,10,13-trimethoxy-5-(4-methoxy-benzyloxy)-4,6,8,12-tetramethyl-trideca-2,6-dien-1-ol 
• 170707-67-2 (2E,4Z,8E)-(6S,7R,10S,11R,12S,14S,15R)-15-(3-Amino-2,5-dimethoxy-phenyl)-11,12,15-trimethoxy-7-(4-methoxy-benzyloxy)-2,6,8,10,14-pentamethyl-pentadeca-2,4,8-trienoic acid 
• 170707-64-9 (2Z,6E)-(4S,5R,8S,9R,10S,12S,13R)-13-(2,5-Dimethoxy-3-nitro-phenyl)-9,10,13-trimethoxy-5-(4-methoxy-benzyloxy)-4,6,8,12-tetramethyl-trideca-2,6-dienal 
• 206661-19-0 (4E,6Z,10E)-(8S,9R,12S,13R,14S,16S,17R)-13,14,17,20,22-Pentamethoxy-9-(4-methoxy-benzyloxy)-4,8,10,12,16-pentamethyl-2-aza-bicyclo[16.3.1]docosa-1⁽²²⁾,4,6,10,18,20-hexaen-3-one 
• 170707-61-6 (E)-(2R,3R,6S,7R,8S,10S,11R)-11-(2,5-Dimethoxy-3-nitro-phenyl)-7,8,11-trimethoxy-3-(4-methoxy-benzyloxy)-2,4,6,10-tetramethyl-undec-4-enal 
• 138694-20-9 Ethyl (2E,4S,5R,6E)-5-Methoxy-2,4-dimethyl-7-phenyl-2,6-heptadienoate 
• 138694-28-7 Methyl (2E,4Z,6S,7R,8E,10S,11R,12S,14S,15R)-7-(tert-Butyldimethylsiloxy)-15-(2,5-dimethoxy-3-nitrophenyl)-11,12,15-trimethoxy-2,6,8,10,14-pentamethyl-2,4,8-pentadecatrienoate 
• 1026339-86-5 (2R,3R,4E,6S,7R,10S,11R)-3-(tert-Butyldimethylsilyloxy)-11-(2,5-dimethoxy-3-nitrophenyl)-N,7,11-trimethoxy-N,2,4,6,10-pentamethyl-8-oxo-9-<(2-thioxo-3-thiazolidinyl)carbonyl>-4-undecenamide 
• 138721-95-6 (2R,3R,4E,6S,7R,10S,11R)-3-(tert-Butyldimethylsilyloxy)-11-(2,5-dimethoxy-3-nitrophenyl)-8-hydroxy-N,7,11-trimethoxy-N,2,4,6,10-pentamethyl-9-<(2-thioxo-3-thiazolidinyl)carbonyl>-4-undecenamide 

Downstream Products

• 74804-36-7 (E)-2-Methyl-4-oxo-but-2-enoic acid {5-[3-(5-acetyl-3-methoxy-4-methyl-tetrahydro-furan-2-yl)-1-methoxy-2-methyl-propyl]-3,6-dioxo-cyclohexa-1,4-dienyl}-amide 
• 73341-73-8 Carbamic acid (4E,6Z,10E)-20,22-dihydroxy-13,14,17-trimethoxy-4,8,10,12,16-pentamethyl-3-oxo-2-aza-bicyclo[16.3.1]docosa-1⁽²²⁾,4,6,10,18,20-hexaen-9-yl ester 
• 74846-02-9 macbecin II diacetate 
• 73341-73-8 macbecin II 

Relevant academic research and scientific papers

Total synthesis of macbecin I

(Chemical Presented) Beyond the bounds of biosynthesis: In a step towards the goal of developing a synthetic pathway for the production of collections of complex molecules related to the benzoquinone ansamycin antibiotics, a natural member of this class w

Chiral crotylsilane-based approach to benzoquinoid ansamycins: Total synthesis of (+)-macbecin I

A highly convergent total synthesis of the antitumor antibiotic (+)- macbecin I (1) has been achieved through the homologation of the aldehyde 3 (C5-C21 aromatic fragment) to the E, Z-dienoate 2 by employing a sequential olefination strategy. Subsequent m

Total Synthesis of (+)-Macbecin I

The first total enantiospecific synthesis of (+)-macbecin I has been performed in a convergent manner by coupling the epoxide (3) with a higher order cyanocuprate derived from the vinyl iodide (46).The required absolute stereochemistries at C(20)-C(21) and C(12)-C(13) were accessible by enantioselective aldol condensations while that at C(16)-C(17) was achieved by Sharpless epoxidation of a secondary (E)-allylic alcohol (39), efficiently prepared by reaction of the aldehyde (37) with CrCl2-CH3CHI2.The remaining stereocentre at C-18 was introduced by an asymmetric hydroxylation of an enolate.Macrocyclization of the amino acid (59) to give the lactam (60) was successfully achieved by its reaction with either 2-mesitylenesulphonyl chloride or bis(2-oxo-3-oxazolidinyl)phosphinic chloride.Incorporation of the carbamate functionality was achieved by reaction of the parent hydroxy derivative with sodium cyanate and trifluoroacetic acid.The final oxidation to the quinone was accomplished with cerium(IV) ammonium nitrate.

The Total Synthesis of (+)-Macbecin I

Reaction of a higher order cyanocuprate, derived from a vinyl iodide, with a chiral epoxide has been used as the basis of the first total enantioselective synthesis of (+)-macbecin I.