neodidemnimide A | 244086-65-5

• 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: neodidemnimide A
• 英文别名: 3-[4-(1H-imidazol-2-yl)-2,5-dioxo-2,5dihydro-1H-pyrrol-3-yl]indole；3-(1H-imidazol-2-yl)-4-(1H-indol-3-yl)pyrrole-2,5-dione
• CAS: 244086-65-5
• 化学式: C₁₅H₁₀N₄O₂
• 分子量: 278.27
• InChiKey: IFELVNLBXMWXQG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  90.6
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  neodidemnimide A 在 钯 作用下， 以 硝基苯 为溶剂， 反应 8.0h， 以75%的产率得到Isogranulatimide 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
• 作为产物：
  描述：

  3-吲哚乙酰胺 在 potassium tert-butylate 、 三溴化硼 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 neodidemnimide A
  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

• 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.
• Aryl[ a ]pyrrolo[3,4- c ]carbazoles as selective cyclin D1-CDK4 inhibitors
  作者：Concha Sanchez-Martinez、Chuan Shih、Margaret M. Faul、Guoxin Zhu、Michael Paal、Carmen Somoza、Tiechao Li、Christine A. Kumrich、Leonard L. Winneroski、Zhou Xun、Harold B. Brooks、Bharvin K.R. Patel、Richard M. Schultz、Tammy B. DeHahn、Charles D. Spencer、Scott A. Watkins、Eileen Considine、Jack A. Dempsey、Catherine A. Ogg、Robert M. Campbell、Bryan A. Anderson、Jill Wagner

  DOI：10.1016/s0960-894x(03)00791-1

  日期：2003.11

  The synthesis of new analogues of Arcyriaflavin A in which one indole ring is replaced by an aryl or heteroaryl ring is described. These new series of aryl[a]pyrrolo[3,4-c]carbazoles were evaluated as inhibitors of Cyclin D1-CDK4. A potent and selective D1-CDK4 inhibitor, 7a (D1-CDK4 IC50=45 nM), has been identified. The potency, selectivity profile against other kinases, and structure-activity relationship (SAR) trends of this class of compounds are discussed. (C) 2003 Elsevier Ltd. All rights reserved.
• 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.