162465-29-4

Upstream product

• 219606-79-8 tert-butyl (2E,5S,6R,7E)-5-{[tert-butyl(dimethyl)silyl]oxy}-6-methyl-8-phenylocta-2,7-dienoate 
• 276870-03-2 (2R,4S,5R,6E)-5-methyl-7-phenyl-hept-6-ene-1,2,4-triol 
• 642087-12-5 (E)-(3S,4R)-3-Hydroxy-4-methyl-6-phenyl-hex-5-enal 
• 220554-70-1 (2E,5S,6R,7E)-5-hydroxy-6-methyl-8-phenylocta-2,7-dienoic acid methyl ester 
• 135758-87-1 (1S,2E)-benzoic acid 1-methyl-3-phenylallyl ester 
• 81176-43-4 (S)-trans-4-phenyl-3-buten-2-ol 
• 208581-50-4 (3S,4R,5E)-3-{[tert-butyl(dimethyl)silyl]oxy}-4-methyl-6-phenylhex-5-en-1-ol 
• 162465-27-2 (3S,4R,5E)-3-[(tert-butyldimethylsilyl)oxy]-4-methyl-6-phenyl-5-hexenal 
• 162465-28-3 (5S)-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-(6R)-methyl-8-phenyl-(2E,7E)-octadienoic acid methyl ester 

Downstream Products

• 162465-32-9 (R)-2-[(2E,7E)-(5S,6R)-5-(tert-Butyl-dimethyl-silanyloxy)-6-methyl-8-phenyl-octa-2,7-dienoylamino]-3-(4-methoxy-phenyl)-propionic acid 2,2,2-trichloro-ethyl ester 
• 162599-94-2 (R)-2-[(2E,7E)-(5S,6R)-5-(tert-Butyl-dimethyl-silanyloxy)-6-methyl-8-phenyl-octa-2,7-dienoylamino]-3-(3-chloro-4-methoxy-phenyl)-propionic acid 2,2,2-trichloro-ethyl ester 
• 240428-60-8 N-<(1,1-dimethylethoxy)carbonyl>-2,2-dimethyl-β-alanyl-(2S)-2-hydroxy-(4-methylpentanoyl)-(2E,5S,6R,7E)-5-hydroxy-6-methyl-8-phenyl-2,7-octadienoyl-4-amino-3-chloro-D-phenylalanine 
• 240428-59-5 N-<(1,1-dimethylethoxy)carbonyl>-2,2-dimethyl-β-alanyl-(2S)-2-hydroxy-4-(methylpentanoyl)-(2E,5S,6R,7E)-5-hydroxy-6-methyl-8-phenyl-2,7-octadienoyl-3-chloro-D-tyrosine 
• 240428-61-9 N-<(1,1-dimethylethoxy)carbonyl>-2,2-dimethyl-β-alanyl-(2S)-2-hydroxy-(4-methylpentanoyl)-(2E,5S,6R,7E)-5-hydroxy-6-methyl-8-phenyl-2,7-octadienoyl-3-hydroxy-D-tyrosine 
• 240428-63-1 N-<(1,1-dimethylethoxy)carbonyl>-2,2-dimethyl-β-alanyl-(2S)-2-hydroxy-4-(methylpentanoyl)-(2E,5S,6R,7E)-5-hydroxy-6-methyl-8-phenyl-2,7-octadienoyl-3-(2-naphthalenyl)-D-alanine 
• 240428-62-0 N-<(1,1-dimethylethoxy)carbonyl>-2,2-dimethyl-β-alanyl-(2S)-2-hydroxy-4-(methylpentanoyl)-(2E,5S,6R,7E)-5-hydroxy-6-methyl-8-phenyl-2,7-octadienoyl-3-(1-naphthalenyl)-D-alanine 
• 240428-58-4 N-<(1,1-dimethylethoxy)carbonyl>-2,2-dimethyl-β-alanyl-(2S)-2-hydroxy-4-(methylpentanoyl)-(2E,5S,6R,7E)-5-hydroxy-6-methyl-8-phenyl-2,7-octadienoyl-4-iodo-D-phenylalanine 
• 240428-52-8 N-<(1,1-dimethylethoxy)carbonyl>-2,2-dimethyl-β-alanyl-(2S)-2-hydroxy-4-(methylpentanoyl)-(2E,5S,6R,7E)-5-hydroxy-6-methyl-8-phenyl-2,7-octadienoyl-3-cyclohexyl D-alanine 
• 240428-57-3 N-<(1,1-dimethylethoxy)carbonyl>-2,2-dimethyl-β-alanyl-(2S)-2-hydroxy-4-(methylpentanoyl)-(2E,5S,6R,7E)-5-hydroxy-6-methyl-8-phenyl-2,7-octadienoyl-4-amino-D-phenylalanine 
• 240428-56-2 N-<(1,1-dimethylethoxy)carbonyl>-2,2-dimethyl-β-alanyl-(2S)-2-hydroxy-4-(methylpentanoyl)-(2E,5S,6R,7E)-5-hydroxy-6-methyl-8-phenyl-2,7-octadienoyl-D-tyrosine 
• 240428-54-0 N-<(1,1-dimethylethoxy)carbonyl>-2,2-dimethyl-β-alanyl-(2S)-2-hydroxy-4-(methylpentanoyl)-(2E,5S,6R,7E)-5-hydroxy-6-methyl-8-phenyl-2,7-octadienoyl-O-(phenylmethyl)-D-serine 
• 240428-53-9 1-(1,1-dimethylethyl)-(7S,10S,12E,16R)-4,4-dimethyl-10-<(1R,2E)-1-methyl-3-phenyl-2-propenyl>-7-(2-methylpropyl)-5,8,14-trioxo-16-(2-phenylethyl)-6,9-dioxa-2,15-diazaheptadec-12-enedioate 
• 188346-52-3 (2R)-N-<(1,1-dimethylethoxy)carbonyl>-2,2-dimethyl-β-alanyl-(2S)-2-hydroxy-4-(methylpentanoyl)-(2E,5S,6R,7E)-5-hydroxy-6-methyl-8-phenyl-2,7-octadienoyl-2-(4-hydroxyphenyl)glycine 

Relevant academic research and scientific papers

Synthesis of cryptothilone 1, the first cryptophycin-epothilone hybrid

A hybrid structure was synthesized in which one portion is characteristic of a cryptophycin and a second sector bears the signature of an epothilone. The hybrid, in contrast to parent cryptophycin and epothilone systems, showed no effect on the tubulin as

Cryptophycin compounds

The present invention provides cryptophycin compounds of Formula I that are useful in the treatment of neoplasms.

Cryptophycins from synthesis

A cryptophycin compound is provided having the structure: Further provided are methods of producing cryptophycins by total synthesis and methods of using cryptophycins in pharmaceuticals. It is a further object of this invention to use cryptophycins to inhibit the proliferation of mammalian cells. Moreover, methods of using cryptophycins to treat neoplasia is also provided.

A synthesis of cryptophycin 4 using a planar chiral molybdenum cationic complex

A synthesis of cytotoxic agent Cryptophycin 4 features a new approach to (5S,6R)-5-hydroxy-6-methyl-8-phenyl-(2E,7E)-dienoic acid in which the anti stereochemistry between two stereogenic centres is secured by addition of a 1,3-dioxan-4-ylcopper(I) reagen

Novel cryptophycin antitumor agents: Synthesis and cytotoxicity of fragment 'B' analogues

A general synthetic approach to novel cryptophycin analogues 6 is described. N-Hydroxysuccinimide active ester 15, a key common intermediate, was converted to β-epoxide 6 in three steps, via initial coupling with unprotected amino acid 9, followed by deprotection/macrolactamization of acyclic precursor 16, and final oxidation of styrene 7 to install the C7-C8 β-epoxide. Cryptophycin styrenes 7 and β-epoxides 6, bearing diverse side chains in fragment 'B', were evaluated for cytotoxic activity, β-Epoxides 6, in general, were significantly more potent than the corresponding α-epoxides 17 and styrenes 7. A benzyl side chain was required for potent activity, with β-epoxide 6u, possessing a 3-Cl,4-(dimethylamino)benzyl moiety, as the most potent cytotoxic agent prepared, with an IC50 = 54 pM, only 2-fold-less than that of Cryptophycin-52 (3).

Total synthesis of cryptophycins. Revision of the structures of cryptophycins A and C

The convergent total synthesis of cryptophycins C and D is described. It has been shown that in both natural products the absolute configuration of the α-amino acid corresponds to the D-series. The structural assignment for cryptophycin C has been correct