cryptophycin-31 | 171674-92-3

• 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-31
• 英文别名: Cryptophycin 31；(3S,6R,10R,13E,16S)-10-[(3,5-dichloro-4-methoxyphenyl)methyl]-6-methyl-3-(2-methylpropyl)-16-[(1S)-1-[(2R,3R)-3-phenyloxiran-2-yl]ethyl]-1,4-dioxa-8,11-diazacyclohexadec-13-ene-2,5,9,12-tetrone
• CAS: 171674-92-3
• 化学式: C₃₅H₄₂Cl₂N₂O₈
• 分子量: 689.633
• InChiKey: JZEHVSOMRIGJDV-GBGDOJRGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  47
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  133
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  cryptophycin-31 在 氢溴酸 、 溶剂黄146 、 锌 作用下， 生成 (E)-(3S,6R,10R,16S)-10-(3,5-Dichloro-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
  参考文献：
  名称：

  Three New Cryptophycins from Nostoc sp. GSV 224

  摘要：

  Cryptophycin 46 (2), -175 (3), and -176 (4) have been identified as three new trace constituents of Nostoc sp. GSV 224. Cryptophycin-46 is an epimer of cryptophycin-3 (5) and to date is the only naturally occurring analogue having the S configuration at C-10 (C-2 in Unit B). Cryptophycins-175 and -176 also differ in unit B where 3 is the O-methyl analogue of cryptophycin-45 (6) and 4 is the O-desmethyl analogue of cryptophycin-21 (8). The relative and absolute stereochemistries of the three new analogues have been related to known cryptophycins by synthesis.

  DOI：

  10.1021/np960700a
• 作为产物：
  描述：

  cryptophycin 3 在 盐酸 、 间氯过氧苯甲酸 作用下， 以 乙二醇二甲醚 、 二氯甲烷 为溶剂， 反应 22.0h， 生成 cryptophycin-31
  参考文献：
  名称：

  Isolation and Structure Determination of Cryptophycins 38, 326, and 327 from the Terrestrial Cyanobacterium Nostoc sp. GSV 224

  摘要：

  Cryptophycin-38 (2), -326 (3), and -327 (4) are three new trace constituents of the terrestrial cyanobacterium Nostoc sp. GSV 224. Cryptophycin-38 is a stereoisomer of cryptophycin-1 (1) and to date is the only naturally occurring analogue that possesses a SS epoxide group in unit A. Cryptophycin-327 is a geometric isomer that differs from 1 in having a cis Delta(2)-double bond in unit A. Cryptophycin-326 is related to cryptophycin-21, but has two chlorines ortho to the methoxy group in unit B. The relative and absolute stereochemistries of 2 have been related to known cryptophycins by semisynthesis and/or spectral analysis.

  DOI：

  10.1021/np0499665

文献信息

• Cryptophycins
  申请人：The University of Hawaii

  公开号：US05955423A1

  公开（公告）日：1999-09-21

  A cryptophycin compound is provided having the structure: ##STR1## Further provided are methods for producing novel cryptophycins from the Nostoc sp. of blue-green algae (cyanobacteria). Pharmaceutical compositions comprising novel cryptophycins are also provided, as are methods for using cryptophycins to inhibit the proliferation of hyperproliferative cells. Further provided are methods for using cryptophycins to inhibit the proliferation of hyperproliferative cells with drug resistant phenotypes, and to treat pathological conditions, such as neoplasia.

  提供了一种具有以下结构的cryptophycin化合物：##STR1## 进一步提供了从蓝藻（蓝细菌）Nostoc sp.中产生新的cryptophycins的方法。还提供了包含新的cryptophycins的制药组合物，以及使用cryptophycins来抑制高增殖细胞的增殖的方法。还提供了使用cryptophycins来抑制具有耐药表型的高增殖细胞的增殖，并治疗病理状况，例如肿瘤的方法。
• Structure determination, conformational analysis, chemical stability studies, and antitumor evaluation of the cryptophycins. Isolation of 18 new analogs from Nostoc sp. strain GSV 224
  作者：Trimurtulu Golakoti、Junichi Ogino、Carl E. Heltzel、Trang Le Husebo、Craig M. Jensen、Linda K. Larsen、Gregory M. L. Patterson、Richard E. Moore、Susan L. Mooberry、Thomas H. Corbett、Frederick A. Valeriote

  DOI：10.1021/ja00154a002

  日期：1995.12.1

  Using a modified isolation procedure devoid of methanol, 18 new cyclic cryptophycins have been isolated from Nostoc sp. GSV 224 as minor constituents in addition to cryptophycins-1 (A), -2 (B), -3 (C), and -4 (D). Acyclic cryptophycins are not found, indicating that the previously reported cryptophycins-5 (E methyl ester), -6 (F methyl ester), and -7 (G) are artifacts produced as a consequence of using methanol in the isolation scheme. Seventeen of the new cyclic analogs differ in structure in either one of the two hydroxy acid units, viz. unit A [(5S,6S,7R,8R)-7,8-epoxy-5-hydroxy-6-methyl-8-phenyl-2(E)-octenoic acid for cryptophycin-1 or (5S,6S)-5-hydroxy-6-methyl-8-phenyl-2(E),7(E)-octadienoic acid for cryptophycin-3] and unit D [(2S)-2-hydroxy-4-methylvaleric acid], or one of the two amino acid units, viz. unit B [(2R)-2-amino-3-(3-chloro-4-methoxyphenyl)propionic acid] and unit C [(2R)3-amino-2-methylpropionic acid], found in the cyclic ABCD peptolide. In unit A of cryptophycins-26, -28, -30, and -40, the methyl group on C-6 is missing or the Delta(2)-double bond is hydrated. In unit B of cryptophycins-16, -17, -23, 31, -43, and -45, the aromatic ring is phenolic and/or possesses two or zero chlorines. In unit C of cryptophycins-21 and -29, the methyl group on C-2 is missing. In unit D of cryptophycins-18, -19, -49, -50, and -54, a different alkyl group (propyl, isopropyl, or sec-butyl) is attached to C-2. Only one of the new analogs, cryptophycin-24, differs in structure for two units by lacking chlorine in unit B and the methyl group in unit C. Revised structures are presented for cryptophycins-5, -6, and -7 and are correlated with cryptophycin-3, the relative stereochemistry of which has been further rigorously established by X-ray crystallography. NOE studies show that the preferred conformations of most cryptophycins in solution differ from the conformation of cryptophycin-3 in the crystal state. Although cryptophycin-1 is relatively stable at pH 7, both in ionic and nonionic media, the ester bond linking units C and D is fairly labile to solvolysis and mild base hydrolysis. Structure-activity relationship studies indicate that the intact macrolide ring, the epoxide group, the chloro and 0-methyl groups in unit B, and the methyl group in unit C are needed for the in vivo activity of cryptophycin-1.
• US06013626
  申请人：——

  公开号：——

  公开（公告）日：——
• Isolation and Structure Determination of Cryptophycins 38, 326, and 327 from the Terrestrial Cyanobacterium <i>Nostoc</i> sp. GSV 224
  作者：Sreedhara Chaganty、Trimurtulu Golakoti、Carl Heltzel、Richard E. Moore、Wesley Y. Yoshida

  DOI：10.1021/np0499665

  日期：2004.8.1

  Cryptophycin-38 (2), -326 (3), and -327 (4) are three new trace constituents of the terrestrial cyanobacterium Nostoc sp. GSV 224. Cryptophycin-38 is a stereoisomer of cryptophycin-1 (1) and to date is the only naturally occurring analogue that possesses a SS epoxide group in unit A. Cryptophycin-327 is a geometric isomer that differs from 1 in having a cis Delta(2)-double bond in unit A. Cryptophycin-326 is related to cryptophycin-21, but has two chlorines ortho to the methoxy group in unit B. The relative and absolute stereochemistries of 2 have been related to known cryptophycins by semisynthesis and/or spectral analysis.
• Three New Cryptophycins from <i>Nostoc</i> sp. GSV 224
  作者：Gottumukkala V. Subbaraju、Trimurtulu Golakoti、Gregory M. L. Patterson、Richard E. Moore

  DOI：10.1021/np960700a

  日期：1997.3.1

  Cryptophycin 46 (2), -175 (3), and -176 (4) have been identified as three new trace constituents of Nostoc sp. GSV 224. Cryptophycin-46 is an epimer of cryptophycin-3 (5) and to date is the only naturally occurring analogue having the S configuration at C-10 (C-2 in Unit B). Cryptophycins-175 and -176 also differ in unit B where 3 is the O-methyl analogue of cryptophycin-45 (6) and 4 is the O-desmethyl analogue of cryptophycin-21 (8). The relative and absolute stereochemistries of the three new analogues have been related to known cryptophycins by synthesis.