6-chloroisatin 3-hydrazone | 879-32-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 6-chloroisatin 3-hydrazone
• 英文别名: 6-chloro-1H-indole-2,3-dione 3-hydrazone；6-chloro-3-hydrazinylindol-2-one
• CAS: 879-32-3
• 化学式: C₈H₆ClN₃O
• 分子量: 195.608
• InChiKey: WWNKLPNAWLOXDA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.95
• 重原子数：
  13.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  67.48
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  6-chloroisatin 3-hydrazone 在 lithium acetate 、 Selectfluor 作用下， 以 1,2-二氯乙烷 为溶剂， 生成 3-fluorooxindole
  参考文献：
  名称：

  方胺催化的3-氟代羟吲哚与吡唑啉酮酮亚胺之间的不对称曼尼希反应。

  摘要：

  已经开发了3-氟代羟吲哚与吡唑啉酮酮亚胺之间的对映选择性曼尼希反应，用于构建含有立体异构CF单元的氨基-吡唑啉酮-羟吲哚。基于允许产生两个相邻的四取代的立体中心的新方案，获得了各种结构多样的氟化氨基吡唑啉酮-羟吲哚，收率高至优异，具有出色的非对映选择性和对映选择性（高达98％的收率，> 20：1博士和> 99％ee）。此外，在克级反应中获得了良好的产率和高的立体选择性。

  DOI：

  10.1039/c9ob01350d
• 作为产物：
  描述：

  Ν-(3-chlorophenyl)-2-hydroxyiminoacetamide 在 硫酸 、 一水合肼 作用下， 以 乙醇 为溶剂， 反应 1.5h， 生成 6-chloroisatin 3-hydrazone
  参考文献：
  名称：

  A cinchona alkaloid catalyzed enantioselective sulfa-Michael/aldol cascade reaction of isoindigos: construction of chiral bispirooxindole tetrahydrothiophenes with vicinal quaternary spirocenters

  摘要：

  对isoindigos进行的对映选择性磺酰-Michael/aldol反应已成功开发，以获得具有邻位季铵螺环中心的双螺环氧吲哚四氢噻吩。

  DOI：

  10.1039/c5ob00774g

文献信息

• Indolinone hydrazides as c-Met inhibitors
  申请人：Koenig Marcel

  公开号：US20060009493A1

  公开（公告）日：2006-01-12

  The present invention relates to compounds of the formulae (I)-(XII), wherein R 1 -R 71 , A, B, X, Y, G, L and Z are defined herein, and their pharmaceutically acceptable salts. These compounds modulate the activity of c-Met and are therefore expected to be useful in the prevention and treatment of c-Met related disorders such as cancer.

  本发明涉及式(I)-(XII)的化合物，其中R1-R71、A、B、X、Y、G、L和Z在此定义，并且它们的药学上可接受的盐。这些化合物调节c-Met的活性，因此预计在预防和治疗与c-Met相关的疾病，如癌症方面有用。
• Electro-organic synthesis of isatins and hydrazones through C–N cross-coupling and C(sp²)–H/C(sp³)–H functionalization
  作者：Neetu Verma、Rajdeep Tyagi、Ashish Khanna、Manisha Malviya、Ram Sagar

  DOI：10.1039/d3ob01128c

  日期：——

  An efficient and electro-organic synthetic approach to synthesize isatin (indole-2,3-dione) from 2-aminoacetophenone supported by I₂–DMSO through C–N cross-coupling and C(sp²)–H/C(sp³)–H functionalization is reported in this communication.

  本通讯报道了一种高效的电有机合成方法，通过 C-N 交叉偶联和 C(sp2)-H/C(sp3)-H 功能化，以 2-氨基苯乙酮为原料，在 I2-DMSO 支持下合成异汀（吲哚-2,3-二酮）。
• Tyrosine Kinase Inhibitors. 3. Structure-Activity Relationships for Inhibition of Protein Tyrosine Kinases by Nuclear-Substituted Derivatives of 2,2'-Dithiobis(1-methyl-N-phenyl-1H-indole-3-carboxamide)
  作者：Gordon W. Rewcastle、Brian D. Palmer、Ellen M. Dobrusin、David W. Fry、Alan J. Kraker、William A. Denny

  DOI：10.1021/jm00039a016

  日期：1994.6

  A series of indole-substituted 2,2'-dithiobis(1-methyl-N-phenyl-1H-indole-3-carboxamides) were prepared and evaluated for their ability to inhibit the tyrosine kinase activity of both the epidermal growth factor receptor (EGFR) and the nonreceptor pp60(v-src) tyrosine kinase. The compounds were synthesized by conversion of appropriate 1-methyloxindoles to 1-methyl-2-indolinethiones with P2S5 followed by subsequent reaction with NaH and phenyl isocyanate and oxidative dimerization of the resulting 2,3-dihydro-N-phenyl-2-thioxo-1H-indole-3-carboxamides. The parent compound and many of the substituted analogues were moderately potent inhibitors of both kinase enzymes, but no clear relationships were seen between substitution on the indole ring and inhibitory activity, While 4-substituted compounds were generally inactive, 5-substituted derivatives with electron-withdrawing groups showed inhibitory activity. However, none of the substituted compounds showed significantly better activity than the unsubstituted parent compound. There was generally a good correlation between activity against the EGFR and pp60(v-src) kinases, but several compounds did show some specificity (>20-fold) of inhibition; 5-Cl and 5-Br derivatives preferentially inhibited pp60(v-src), while the 5-CF3 compound preferentially inhibited EGFR. Selected compounds from the series were found to inhibit the growth of Swiss 3T3 fibroblasts with IC(50)s in the range 2-25 mu M, the most active being 4-substituted derivatives. The compounds inhibited bFGF-mediated protein tyrosine phosphorylation in intact cells more effectively than EGFR- or PDGF-mediated phosphorylation.
• Rewcastle Gordon W., Palmer Brian D., Dobrusin Ellen M., Fry David W., Kr+, J. Med. Chem, 37 (1994) N 13, S 2033-2042
  作者：Rewcastle Gordon W., Palmer Brian D., Dobrusin Ellen M., Fry David W., Kr+

  DOI：——

  日期：——
• INDOLINONE HYDRAZIDES AS C-MET INHIBITORS
  申请人：Sugen, Inc.

  公开号：EP1644362A2

  公开（公告）日：2006-04-12