6-苄氧基-1,3-二氢吲哚-2-酮 | 458526-08-4

• 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
• 中文名称: 6-苄氧基-1,3-二氢吲哚-2-酮
• 中文别名: 6-苄氧基吲哚酮
• 英文名称: 6-(benzyloxy)indolin-2-one
• 英文别名: 6-benzyloxyoxindole；6-Benzyloxy-1,3-dihydro-indol-2-one；6-phenylmethoxy-1,3-dihydroindol-2-one
• CAS: 458526-08-4
• 化学式: C₁₅H₁₃NO₂
• 分子量: 239.274
• InChiKey: MZWXDZCHYCAVBA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2933790090

反应信息

• 作为反应物：
  描述：

  6-苄氧基-1,3-二氢吲哚-2-酮 、 3,5-二甲基-2-吡咯甲醛 以 乙醇 为溶剂， 以89%的产率得到(3Z)-3-[(3,5-dimethyl-1H-pyrrol-2-yl)methylidene]-6-phenylmethoxy-1H-indol-2-one
  参考文献：
  名称：

  Synthesis and evaluation of prodrugs for anti-angiogenic pyrrolylmethylidenyl oxindoles

  摘要：

  Potential prodrugs of inhibitors of VEGF-induced angiogenesis have been investigated. The prodrug systems studied were the 4-nitrobenzyl, 2-nitrophenylacetyl and 3-methyl-3-(3,6-dimethylbenzo-1,4-quinon-2-yl)butanoyI groups, readily attached to acidic OH or NH groups in drug molecules, and released upon bioreductive activation. The anti-angiogenic compounds studied were the pyrrolylmethylidenyl oxindole SU5416 (semaxanib) and its novel 6-hydroxy derivative. The potentially pro-anti-angiogenic compounds were assayed for their ability to block VEGF-induced angiogenesis in HUVECS in comparison to the free agents. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.12.108
• 作为产物：
  描述：

  6-羟基吲哚啉-2-酮 、 溴甲苯 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 6-苄氧基-1,3-二氢吲哚-2-酮
  参考文献：
  名称：

  [EN] AMINE-LINKED C3-GLUTARIMIDE DEGRONIMERS FOR TARGET PROTEIN DEGRADATION
  [FR] DÉGRONIMÈRES DE C3-GLUTARIMIDE LIÉS À UNE AMINE POUR LA DÉGRADATION DE PROTÉINES CIBLES

  摘要：

  这项发明提供了胺连接的C3-戊二酰亚胺Degronimers和Degrons，用于治疗应用，如本文进一步描述的，以及它们的使用方法、组合物以及它们的制备方法。

  公开号：

  WO2017197051A1

文献信息

• Indolone derivatives having vascular damaging activity
  申请人：——

  公开号：US20040147589A1

  公开（公告）日：2004-07-29

  This invention relates to the use of compounds of Formula (I) as vascular damaging agents: wherein X is selected from: —O—, —S—, —S(O)—, —S(O 2 )—, —N(R 5 )—, —C(O)—, —C(O)N(R 5 )—, —N(R 5 )C(O)—, —S(O2)N(R 5 )—, or —N(R 5 )S(O 2 )—; R 1 is independently selected from: amino, halo, hydroxy, —OPO 3 H 2 , C 1-4 alkyl, or C 1-4 alkoxy, wherein the amino group is optionally substituted by an amino acid residue and the hydroxy group is optionally esterified; R 2 is selected from: hydrogen or C 1-4 alkyl; R 3 is selected from: hydrogen, halo, hydroxy, hydroxyC 1-4 alkyl, cyano, cyanoC 1-4 alkyl, carboxy, carboxyC 1-4 alkyl, C 1-4 alkanoyl, C 1-4 alkanoylC 1-4 alkyl, carbamoyl, carbamoylC 1-4 alkyl, C 1-4 alkoxy, C 1-4 alkoxycarbonyl, C 1-4 alkoxycarbonylC 1-4 alkyl, C 1-4 alkoxycarbonylamino, amino, N-C 1-4 alkylamino, NN-diC 1-4 alkylamino, aminoC 1-4 alkyl, N-C 1-4 alkylaminoC 1-4 alkyl, NN-diC 1-4 alkylaminoC 1-4 alkyl, ureido, or C 1-4 alkylureyleno; R 4 is independently selected from: C 1-4 alkyl, C 1-4 alkoxy or halo; R 5 is selected from: hydrogen or C 1-4 alkyl; n is 0 or 1; p is 0, 1, 2 or 3; and q is 0, 1 or 2; or a salt, pro-drug or solvate thereof. The invention also relates to novel compounds of Formula (I) and to processes for the preparation of compounds of Formula (I). 1

  本发明涉及使用式（I）化合物作为血管损伤剂的方法：其中X选择自：—O—，—S—，—S（O）—，—S（O2）—，—N（R5）—，—C（O）—，—C（O）N（R5）—，—N（R5）C（O）—，—S（O2）N（R5）—或—N（R5）S（O2）—；R1独立选择自：氨基，卤素，羟基，—OPO3H2，C1-4烷基或C1-4烷氧基，其中氨基团可以选择性地被氨基酸残基取代，羟基可以选择性地酯化；R2选择自：氢或C1-4烷基；R3选择自：氢，卤素，羟基，羟基C1-4烷基，氰基，氰基C1-4烷基，羧基，羧基C1-4烷基，C1-4酰基，C1-4酰基C1-4烷基，氨基甲酰基，氨基甲酰基C1-4烷基，C1-4烷氧基，C1-4烷氧羰基，C1-4烷氧羰基C1-4烷基，C1-4烷氧羰基氨基，氨基，N-C1-4烷基氨基，NN-二C1-4烷基氨基，氨基C1-4烷基，N-C1-4烷基氨基C1-4烷基，NN-二C1-4烷基氨基C1-4烷基，脲基或C1-4烷基脲基；R4独立选择自：C1-4烷基，C1-4烷氧基或卤素；R5选择自：氢或C1-4烷基；n为0或1；p为0、1、2或3；q为0、1或2；或其盐、前药或溶剂。本发明还涉及式（I）的新化合物以及制备式（I）化合物的方法。
• Synthesis of potential prodrug systems for reductive activation. Prodrugs for anti-angiogenic isoflavones and VEGF receptor tyrosine kinase inhibitory oxindoles
  作者：Emilie A. Blanche、Lesley Maskell、Marie A. Colucci、Jacqueline L. Whatmore、Christopher J. Moody

  DOI：10.1016/j.tet.2009.04.014

  日期：2009.6

  A number of potential prodrug systems for reductive activation have been investigated. The prodrug systems chosen for the study were the 2-nitrophenylacetyl, 3-methyl-3-(3,6-dimethyl-1,4-benzoquinon-2-yl)butanoyl and 4-nitrobenzyl groups, readily attached to acidic OH or NH groups in drug molecules, and released upon bioreductive activation. The drug molecules studied were the naturally occurring isoflavone biochanin A, an inhibitor of VEGF-induced angiogenesis, and the pyrrolylmethylidenyl oxindole SU5416 (semaxanib) and its 6-hydroxy derivative, inhibitors of VEGF receptor tyrosine kinase. Following coupling the prodrug system to the drug, the compounds were evaluated chemically and biologically. Under chemical reducing conditions, the 3-methyl-3-(3,6-dimethyl-1,4-benzoquinon-2-yl)butanoic acid based prodrugs appear to fragment the most efficiently, followed by the 2-nitrophenylacetate esters with the 4-nitrobenzyl ethers being the least efficient. The potentially pro-anti-angiogenic compounds were also assayed for their ability to block VEGF-induced angiogenesis in HUVECS in comparison to the free agents. Control compounds that cannot be activated under bioreductive conditions are less potent than the free drug, whereas many of the potential prodrugs not only exhibit a dose response, but appear at least equipotent with the free drug. (C) 2009 Elsevier Ltd. All rights reserved.
• INDOLONE DERIVATIVES HAVING VASCULAR-DAMAGING ACTIVITY
  申请人：AstraZeneca AB

  公开号：EP1370527A1

  公开（公告）日：2003-12-17
• AMINE-LINKED C3-GLUTARIMIDE DEGRONIMERS FOR TARGET PROTEIN DEGRADATION
  申请人：C4 Therapeutics, Inc.

  公开号：EP3455219A1

  公开（公告）日：2019-03-20
• US7186745B2
  申请人：——

  公开号：US7186745B2

  公开（公告）日：2007-03-06