didemnimide C | 186144-21-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: didemnimide C
• 英文别名: 3-(1H-indol-3-yl)-4-(3-methylimidazol-4-yl)pyrrole-2,5-dione
• CAS: 186144-21-8
• 化学式: C₁₆H₁₂N₄O₂
• 分子量: 292.297
• InChiKey: WVAGDTBMSZAWPO-UHFFFAOYSA-N

物化性质

• 熔点：
  >300 °C (decomp)
• 沸点：
  672.9±55.0 °C(Predicted)
• 密度：
  1.50±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  79.8
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  didemnimide C 在 palladium on activated charcoal 作用下， 以 乙腈 为溶剂， 反应 3.5h， 以64%的产率得到17-methylgranulatimide
  参考文献：
  名称：

  Improved Synthesis of Isogranulatimide, a G2 Checkpoint Inhibitor. Syntheses of Didemnimide C, Isodidemnimide A, Neodidemnimide A, 17-Methylgranulatimide, and Isogranulatimides A−C

  摘要：

  A concise, improved synthesis of isogranulatimide (6), a naturally occurring substance with G2 checkpoint inhibition activity, is described. Also reported are the syntheses of didemnimide C (18), isodidemnimide A (24), neodidemnimide A (36), 17-methylgranulatimide (9), and isogranulatimides A (10), B (11), and C (12). Compounds 9-12, congeners of isogranulatimide (6), are now available for biological evaluation.

  DOI：

  10.1021/jo9914723
• 作为产物：
  描述：

  3-吲哚乙酰胺 在 4 A molecular sieve 、 potassium tert-butylate 、 镍 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 49.0h， 生成 didemnimide C
  参考文献：
  名称：

  Improved Synthesis of Isogranulatimide, a G2 Checkpoint Inhibitor. Syntheses of Didemnimide C, Isodidemnimide A, Neodidemnimide A, 17-Methylgranulatimide, and Isogranulatimides A−C

  摘要：

  A concise, improved synthesis of isogranulatimide (6), a naturally occurring substance with G2 checkpoint inhibition activity, is described. Also reported are the syntheses of didemnimide C (18), isodidemnimide A (24), neodidemnimide A (36), 17-methylgranulatimide (9), and isogranulatimides A (10), B (11), and C (12). Compounds 9-12, congeners of isogranulatimide (6), are now available for biological evaluation.

  DOI：

  10.1021/jo9914723

文献信息

• Synthesis and cyclisation of didemnimide C and its imidazol-1-yl isomer
  作者：Andreas Terpin、Christian Winklhofer、Susanne Schumann、Wolfgang Steglich

  DOI：10.1016/s0040-4020(97)10410-0

  日期：1998.2

  A key step in the synthesis of the marine alkaloid didemnimide C (Ic) is the Stille coupling between the urethane protected 3-bromo-4-(indol-3-yl)-1-methylmaleimide 3 and 5-tributylstannyl-1-methylimidazole (4). In this manner 1c can be obtained in four steps in 29% overall yield. Treatment of 3 with imidazolyl magnesium bromide affords the imidazol-1-yl compound 7 which can then be converted to the cycle derivatives 8 and 10 upon irradiation with a halogen lamp. (C) 1998 Elsevier Science Ltd. All rights reserved.
• GRANULATIMIDE DERIVATIVES FOR USE IN CANCER TREATMENT
  申请人：THE UNIVERSITY OF BRITISH COLUMBIA

  公开号：EP1070068A1

  公开（公告）日：2001-01-24
• US6291447B1
  申请人：——

  公开号：US6291447B1

  公开（公告）日：2001-09-18
• [EN] GRANULATIMIDE DERIVATIVES FOR USE IN CANCER TREATMENT<br/>[FR] DERIVES DE GRANULATIMIDE UTILISES DANS LE TRAITEMENT DU CANCER
  申请人：THE UNIVERSITY OF BRITISH COLUMBIA

  公开号：WO1999047522A1

  公开（公告）日：1999-09-23

  (EN) Novel granulatimide compounds and pharmaceutical formulations thereof are provided. Compounds of this invention have general formula (I) or (II) wherein are independently R or Z as defined below, or in combination F and F' is Ar1 as defined below; Ar1 is a monocyclic, bicyclic or tricyclic, fully or partially aromatic system containing five or six membered carbocyclic or, oxygen, nitrogen or sulphur containing heterocyclic rings, optionally substituted with R or Z; W is selected from the group consisting of formula (i); (ii) or (iii), wherein the structures are as described in: (i), (ii) and (iii). R and Z are optional substituents as defined in the application.(FR) L'invention concerne de nouveaux composés de granulatimide et des formulations pharmaceutiques de ceux-ci. Les composés de l'invention sont représentés par la formule (I) ou (II). Dans cette formule, F et F' représentent indépendamment R ou Z tels que définis ci-dessous, ou F et F' en combinaison représentent Ar1 tel que défini ci-dessous; Ar1 représente un système monocyclique, bicyclique ou tricyclique partiellement ou totalement aromatique, contenant des noyaux carbocycliques à cinq ou six éléments, ou de l'oxygène, de l'azote ou du soufre comprenant des noyaux hétérocycliques, éventuellement substitués par R ou Z; W est sélectionné dans le groupe constitué par les formules (i), (ii) ou (iii), les structures étant telles que ci-dessous.
• Improved Synthesis of Isogranulatimide, a G2 Checkpoint Inhibitor. Syntheses of Didemnimide C, Isodidemnimide A, Neodidemnimide A, 17-Methylgranulatimide, and Isogranulatimides A−C
  作者：Edward Piers、Robert Britton、Raymond J. Andersen

  DOI：10.1021/jo9914723

  日期：2000.1.1

  A concise, improved synthesis of isogranulatimide (6), a naturally occurring substance with G2 checkpoint inhibition activity, is described. Also reported are the syntheses of didemnimide C (18), isodidemnimide A (24), neodidemnimide A (36), 17-methylgranulatimide (9), and isogranulatimides A (10), B (11), and C (12). Compounds 9-12, congeners of isogranulatimide (6), are now available for biological evaluation.

表征谱图