cryptophycin F | 155379-98-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 英文名称: cryptophycin F
• 英文别名: cryptophycin-12；(2R)-3-[[(2S)-3-(3-chloro-4-methoxyphenyl)-2-[[(E,5S,6S,7R,8S)-5,7,8-trihydroxy-6-methyl-8-phenyloct-2-enoyl]amino]propanoyl]amino]-2-methylpropanoic acid
• CAS: 155379-98-9
• 化学式: C₂₉H₃₇ClN₂O₈
• 分子量: 577.074
• InChiKey: LMWKOYOHPNYYLI-WXPDOMMMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  40
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  165
• 氢给体数：
  6
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 cryptophycin F 生成 cryptophycin F methyl ester
  参考文献：
  名称：

  Total Structures of Cryptophycins, Potent Antitumor Depsipeptides from the Blue-Green Alga Nostoc sp. Strain GSV 224

  摘要：

  Cryptophycin (A,1), the major cytotoxin in the blue-green alga (cyanobacterium) Nostoc sp. GSV 224, shows excellent activity against solid tumors implanted in mice. This cyclic depsipeptide had previously been isolated from Nostoc sp. ATCC 53789 as an antifungal agent and its gross structure determined by researchers at Merck. The relative and absolute stereochemistry of this potentially important drug has now been established using a combination of chemical and spectral techniques. Six minor cryptophycins (B-G, 2-7) have also been isolated from GSV 224 and their total structures and cytotoxicities determined. Two types of cryptophycins are present in this alga, the major series possessing a monochlorinated L-O-methyltyrosine unit and the minor series possessing a nonchlorinated D-O-methyltyrosine unit. Structure-activity relationship (SAR) studies of the cryptophycins and several derivatives and degradation products (8-14) are described. Also presented are preliminary in vivo results far cryptophycin A against six solid tumors.

  DOI：

  10.1021/ja00090a020
• 作为产物：
  描述：

  (E)-(3S,6R,10S,16S)-10-(3-Chloro-4-methoxy-benzyl)-3-isobutyl-6-methyl-16-((E)-(R)-1-methyl-3-phenyl-allyl)-1,4-dioxa-8,11-diaza-cyclohexadec-13-ene-2,5,9,12-tetraone 在 sodium hydroxide 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 101.0h， 生成 cryptophycin F
  参考文献：
  名称：

  Total Structures of Cryptophycins, Potent Antitumor Depsipeptides from the Blue-Green Alga Nostoc sp. Strain GSV 224

  摘要：

  Cryptophycin (A,1), the major cytotoxin in the blue-green alga (cyanobacterium) Nostoc sp. GSV 224, shows excellent activity against solid tumors implanted in mice. This cyclic depsipeptide had previously been isolated from Nostoc sp. ATCC 53789 as an antifungal agent and its gross structure determined by researchers at Merck. The relative and absolute stereochemistry of this potentially important drug has now been established using a combination of chemical and spectral techniques. Six minor cryptophycins (B-G, 2-7) have also been isolated from GSV 224 and their total structures and cytotoxicities determined. Two types of cryptophycins are present in this alga, the major series possessing a monochlorinated L-O-methyltyrosine unit and the minor series possessing a nonchlorinated D-O-methyltyrosine unit. Structure-activity relationship (SAR) studies of the cryptophycins and several derivatives and degradation products (8-14) are described. Also presented are preliminary in vivo results far cryptophycin A against six solid tumors.

  DOI：

  10.1021/ja00090a020

文献信息

• Total Structures of Cryptophycins, Potent Antitumor Depsipeptides from the Blue-Green Alga Nostoc sp. Strain GSV 224
  作者：Golakoti Trimurtulu、Ikuko Ohtani、Gregory M. L. Patterson、Richard E. Moore、Thomas H. Corbett、Frederick A. Valeriote、Lisa Demchik

  DOI：10.1021/ja00090a020

  日期：1994.6

  Cryptophycin (A,1), the major cytotoxin in the blue-green alga (cyanobacterium) Nostoc sp. GSV 224, shows excellent activity against solid tumors implanted in mice. This cyclic depsipeptide had previously been isolated from Nostoc sp. ATCC 53789 as an antifungal agent and its gross structure determined by researchers at Merck. The relative and absolute stereochemistry of this potentially important drug has now been established using a combination of chemical and spectral techniques. Six minor cryptophycins (B-G, 2-7) have also been isolated from GSV 224 and their total structures and cytotoxicities determined. Two types of cryptophycins are present in this alga, the major series possessing a monochlorinated L-O-methyltyrosine unit and the minor series possessing a nonchlorinated D-O-methyltyrosine unit. Structure-activity relationship (SAR) studies of the cryptophycins and several derivatives and degradation products (8-14) are described. Also presented are preliminary in vivo results far cryptophycin A against six solid tumors.