5,6-methylenedioxy-1-methylindole-3-carbaldehyde | 118726-64-0

• 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: 5,6-methylenedioxy-1-methylindole-3-carbaldehyde
• 英文别名: 5-methyl-5H-[1,3]dioxolo[4,5-f]indole-7-carbaldehyde；5-Methyl-5H-[1,3]dioxolo[4,5-f]indol-7-carbaldehyd；5,6-methylenedioxy-1-methyl-indole-3-carboxaldehyde；5-methyl-[1,3]dioxolo[4,5-f]indole-7-carbaldehyde
• CAS: 118726-64-0
• 化学式: C₁₁H₉NO₃
• 分子量: 203.197
• InChiKey: OKZHOGTULUURPZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  40.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5,6-methylenedioxy-1-methylindole-3-carbaldehyde 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以86%的产率得到3-hydroxymethyl-1-methyl-5,6-methylenedioxyindole
  参考文献：
  名称：

  Synthesis of indolocyclotriveratrylenes

  摘要：

  Indolocyclotriveratrylenes linked through C2 and C3 can be prepared by acid-catalysed reactions of indole-2- or -3-methanols. The initial example, compound 1 has been confirmed, and an X-ray crystal structure is reported. Seven new examples of indolocyclotriveratrylenes, namely 7, 9, 11, 13,17, 28 and 29 are described. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.05.092
• 作为产物：
  描述：

  5-methyl-5H-[1,3]dioxolo[4,5-f]indole 在 N,N-二甲基甲酰胺 、 三氯氧磷 作用下， 生成 5,6-methylenedioxy-1-methylindole-3-carbaldehyde
  参考文献：
  名称：

  Fujisawa, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1959, vol. 79, p. 775

  摘要：

  DOI：

文献信息

• Heterocyclic substituted pyrazolones
  申请人：Cephalon, Inc.

  公开号：US06455525B1

  公开（公告）日：2002-09-24

  The present invention is directed to novel heterocyclic substituted pyrazolones, including pharmaceutical compositions, diagnostic kits, assay standards or reagents containing the same, and methods of using the same as therapeutics. The invention is also directed to intermediates and processes for making these novel compounds.

  本发明涉及新颖的杂环取代吡唑酮，包括含有这些化合物的药物组合物、诊断试剂盒、检测标准或试剂，以及将其用作治疗的方法。该发明还涉及制备这些新化合物的中间体和方法。
• [EN] HETEROCYCLIC SUBSTITUTED PYRAZOLONES<br/>[FR] PYRAZOLONES HETEROCYCLIQUES SUBSTITUES
  申请人：CEPHALON INC

  公开号：WO2001032653A1

  公开（公告）日：2001-05-10

  The present invention is directed to novel heterocyclic substituted pyrazolones, including pharmaceutical compositions, diagnostic kits, assay standards or reagents containing the same, and methods of using the same as therapeutics. The invention is also directed to intermediates and processes for making these novel compounds.

  本发明涉及新型杂环取代吡唑酮化合物，包括制备这些化合物的中间体和方法，以及包含这些化合物的药物组合物、诊断试剂盒、检测标准或试剂，并将其用作治疗的方法。
• Structure-guided identification of novel VEGFR-2 kinase inhibitors via solution phase parallel synthesis
  作者：Rabindranath Tripathy、Alyssa Reiboldt、Patricia A. Messina、Mohamed Iqbal、Jasbir Singh、Edward R. Bacon、Thelma S. Angeles、Shi X. Yang、Mark S. Albom、Candy Robinson、Hong Chang、Bruce A. Ruggeri、John P. Mallamo

  DOI：10.1016/j.bmcl.2006.01.063

  日期：2006.4

  Structural analysis of the essential binding elements of the oxindole-based kinase inhibitor (1) led to the identification of a novel class of heterocyclic-substituted pyrazolones. Knoevenagel condensation of a variety of activated methylene nucleophiles with indole or pyrrole carboxaldehydes provided a focused library of molecules, each containing elements of kinase pharmacophore probe. Initial screening for VEGFR-2 kinase inhibit ion eliminated several of the probes. Identification of ail active pyrazolone motif and further optimization resulted in several highly potent VEGFR-2 inhibitors with cellular efficacy, anti-angiogenic activity ex vivo in rat aortic ring explant cultures, and oral anti-tumor efficacy in nude mice. (C) 2006 Elsevier Ltd. All rights reserved.
• HETEROCYCLIC SUBSTITUTED PYRAZOLONES
  申请人：CEPHALON, INC.

  公开号：EP1226141A1

  公开（公告）日：2002-07-31
• US6455525B1
  申请人：——

  公开号：US6455525B1

  公开（公告）日：2002-09-24