5-chloro-3-methylene-2-oxindole | 442883-74-1

• 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-chloro-3-methylene-2-oxindole
• 英文别名: 5-chloro-3-methyleneoxindole；5-chloro-3-methylidene-1H-indol-2-one
• CAS: 442883-74-1
• 化学式: C₉H₆ClNO
• 分子量: 179.606
• InChiKey: AAFWLOLTFMTFGR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-(4-bromobenzylidene)glycine methyl ester 、 5-chloro-3-methylene-2-oxindole 在 tetrakis(actonitrile)copper(I) hexafluorophosphate 、 (Rp)-2-(tert-butylthio)-1-(diphenylphosphino)ferrocene 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Enantioselective synthesis of the spirotryprostatin A scaffold

  摘要：

  The pentacyclic spirotryprostatin scaffold embodies an oxindole with an all-carbon quaternary stereocenter. The scaffold can efficiently be accessed in a one-pot reaction sequence consisting of a highly enantioselective 1,3-dipolar cycloaddition, N-acylation of the resulting stereochemically complex 3,3'-pyrrolidinyl-spirooxindole core with Fmoc-proline and spontaneous ring closure upon N-deprotection. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.04.056
• 作为产物：
  描述：

  3,3-二溴-5-氯-1,3-二氢吲哚-2-酮 在 三氟化硼乙醚 、 水 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 23.25h， 生成 5-chloro-3-methylene-2-oxindole
  参考文献：
  名称：

  方便地合成3-亚甲基氧吲哚：吲哚-3-乙酸的细胞毒性代谢产物

  摘要：

  3-亚甲基羟吲哚是吲哚-3-乙酸的细胞毒性代谢产物，有可能用于癌症治疗。该物质和环取代的类似物可方便地通过彼得森烯化反应从相应的靛红合成。

  DOI：

  10.1016/s0040-4039(02)00855-9

文献信息

• Reactivity toward Thiols and Cytotoxicity of 3-Methylene-2-oxindoles, Cytotoxins from Indole-3-acetic Acids, on Activation by Peroxidases
  作者：Lisa K. Folkes、Sharon Rossiter、Peter Wardman

  DOI：10.1021/tx025521+

  日期：2002.6.1

  Oxidation of indole-3-acetic acid and its derivatives by peroxidases such as that from horseradish produces many products, including 3-methylene-2-oxindoles. These have long been associated with biological activity, but their reactivity has not been characterized. We have previously demonstrated the potential value of substituted indole acetic acids and horseradish peroxidase as the basis for targeted

  吲哚-3-乙酸及其衍生物被辣根等过氧化物酶氧化后，会产生许多产物，包括3-亚甲基-2-氧吲哚。长期以来，这些都与生物活性有关，但尚未对其反应性进行表征。以前我们已经证明了取代的吲哚乙酸和辣根过氧化物酶作为靶向癌症治疗的基础的潜在价值，因为当观察到高细胞毒性时，化合物被氧化之前具有低细胞毒性。前药和酶的结合会消耗细胞内的硫醇。在这项研究中，合成了在3位，4位，5位或6位被甲基，F或Cl取代的3-亚甲基-2-氧吲哚及其衍生物，它们对代表性的巯基亲核试剂（谷胱甘肽，半胱氨酸，和半胱氨酸肽）使用停止流动力学分光光度法测量。在25°C的pH 7.4下，速率常数在大约2 x 10（3）到2 x 10（4）M（-）（1）s（-）（1）的范围内，这意味着数十倍的寿命这些亚甲基羟吲哚在细胞环境中的传播时间为毫秒，扩散距离为几微米。不出所料，卤素取代降低了辣根过氧化物酶处理中亚甲基羟吲哚的生成速率。使用中国仓
• 3-(4-amidopyrrol-2-ylmethylidene)-2-indolinone der derivatives as protein kinase inhibitors
  申请人：Guan Huiping

  公开号：US20070027149A1

  公开（公告）日：2007-02-01

  The present invention relates to pyrrole substituted 2-indolinone compounds and their pharmaceutically acceptable salts which modulate the activity of protein kinases and therefore are expected to be useful in the prevention and treatment of protein kinase related cellular disorders such as cancer.

  本发明涉及吡咯取代的2-吲哚酮化合物及其药学上可接受的盐，这些化合物调节蛋白激酶的活性，因此预计在预防和治疗蛋白激酶相关的细胞疾病，如癌症方面有用。
• Alantrypinone and its derivatives: Synthesis and antagonist activity toward insect GABA receptors
  作者：Takayuki Watanabe、Mitsuhiro Arisawa、Kenji Narusuye、Mohommad Sayed Alam、Kazumi Yamamoto、Masaaki Mitomi、Yoshihisa Ozoe、Atsushi Nishida

  DOI：10.1016/j.bmc.2008.11.017

  日期：2009.1

  The gamma-aminobutyric acid (GABA) receptor bears important sites of action for insecticides. Alantrypinone is an insecticidal alkaloid that acts as a selective antagonist for housefly (vs rat) GABA receptors, and is considered to be a lead compound for the development of a safer insecticide. In an attempt to obtain compounds with greater activity, a series of racemic alantrypinone derivatives were systematically synthesized using hetero Diels-Alder reactions, and a total of34 compounds were examined for their ability to inhibit the specific binding of [H-3]4'-ethynyl-4-n-propylbicycloorthobenzoate, a high-affinity non-competitive antagonist, to housefly-head membranes. The assay results showed that (1) there is no significant difference between the potencies of natural (+)-alantrypinone and its synthetic racemate; (2) the amide NHs at the 2- and 18-positions are important for high activity; (3) there is a considerable drop in potency for compounds without an aromatic ring at the 16-position; and (4) a large substituent at the 3-position is detrimental to high activity. (c) 2008 Elsevier Ltd. All rights reserved.
• Efficient assembly of 3-substituted oxindole-based isoxazolines leading to the synthesis of (±)-flustraminol-B and related natural product building blocks
  作者：Anand Singh、Gregory P. Roth

  DOI：10.1016/j.tetlet.2012.07.005

  日期：2012.9

  An efficient synthesis of oxindole-based isoxazolines has been developed and the resulting spirocyclic intermediates have been elaborated to synthetically versatile 3-hydroxy-3-alkyl oxindole building blocks such as the 3-hydroxy-3-methylenecyano-2-oxindoles (6) and gamma-amino alcohols (12). Utility of this methodology is demonstrated through the synthesis of pyrrolo[2,3-b]indolines including the marine natural product (+/-)-flustraminol-B. (C) 2012 Elsevier Ltd. All rights reserved.
• A [3 + 2] Dipolar Cycloaddition Route to 3-Hydroxy-3-alkyl Oxindoles: An Approach to Pyrrolidinoindoline Alkaloids
  作者：Anand Singh、Gregory P. Roth

  DOI：10.1021/ol200547m

  日期：2011.4.15

  A [3 + 2] cycloaddition approach to the 3-hydroxy-3-alkyl oxindole scaffold is described. Isoxazolines obtained by cycloaddition of nitrile oxide 3 with 3-methylene oxindoles were elaborated to 3-hydroxy-3-cyanomethyl oxindoles employing a one-pot protocol en route to the pyrrolidinoindoline moiety which is found in many natural products. The total syntheses of alkaloids (+/-)-alline and (+/-)-CPC-1 were achieved using this methodology.