7-Chloro-3-[1-dimethylamino-meth-(Z)-ylidene]-1,3-dihydro-indol-2-one | 1283077-07-5

• 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: 7-Chloro-3-[1-dimethylamino-meth-(Z)-ylidene]-1,3-dihydro-indol-2-one
• 英文别名: (Z/E)-7-chloro-3-((dimethylamino)methylene)indolin-2-one；(3Z)-7-chloro-3-(dimethylaminomethylidene)-1H-indol-2-one
• CAS: 1283077-07-5
• 化学式: C₁₁H₁₁ClN₂O
• 分子量: 222.674
• InChiKey: USWWIUOAUXGJSF-VURMDHGXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-氯-3-碘苯 、 7-Chloro-3-[1-dimethylamino-meth-(Z)-ylidene]-1,3-dihydro-indol-2-one 在 copper(I) bromide 、 sodium hydride 作用下， 生成 7-Chloro-1-(3-chloro-phenyl)-3-[1-dimethylamino-meth-(Z)-ylidene]-1,3-dihydro-indol-2-one
  参考文献：
  名称：

  A novel class of "GABAergic" agents: 1-aryl-3-(aminoalkylidene)oxindoles

  摘要：

  Antagonism of mercaptopropionic acid (MPA) induced convulsions, reflecting a GABAergic mechanism, was observed in a series of 1-aryl-3-(aminoalkylidene)oxindoles. Optimal MPA antagonism was associated with 3-halo, 3-alkyl, and/or 4-alkoxy substituents in the pendant aryl ring and with (dimethylamino)methylene, 1-(dimethylamino)-ethylidene and N-methyl-2-pyrrolidinylidene side chains. The precise mechanism of action of these agents is unclear at this time; however, they are not GABA mimics and they do not affect GABA levels. Like other GABAergic agents, these compounds are potent enhancers of benzodiazepine binding and they antagonize cyclic GMP elevations induced by isoniazid. Compounds from this series may therefore have potential therapeutic utility as anticonvulsants or anxiolytics.

  DOI：

  10.1021/jm00122a025
• 作为产物：
  描述：

  7-氯吲哚酮 、 alkaline earth salt of/the/ methylsulfuric acid 以 氯仿 为溶剂， 以70%的产率得到7-Chloro-3-[1-dimethylamino-meth-(Z)-ylidene]-1,3-dihydro-indol-2-one
  参考文献：
  名称：

  A novel class of "GABAergic" agents: 1-aryl-3-(aminoalkylidene)oxindoles

  摘要：

  Antagonism of mercaptopropionic acid (MPA) induced convulsions, reflecting a GABAergic mechanism, was observed in a series of 1-aryl-3-(aminoalkylidene)oxindoles. Optimal MPA antagonism was associated with 3-halo, 3-alkyl, and/or 4-alkoxy substituents in the pendant aryl ring and with (dimethylamino)methylene, 1-(dimethylamino)-ethylidene and N-methyl-2-pyrrolidinylidene side chains. The precise mechanism of action of these agents is unclear at this time; however, they are not GABA mimics and they do not affect GABA levels. Like other GABAergic agents, these compounds are potent enhancers of benzodiazepine binding and they antagonize cyclic GMP elevations induced by isoniazid. Compounds from this series may therefore have potential therapeutic utility as anticonvulsants or anxiolytics.

  DOI：

  10.1021/jm00122a025

文献信息

• Design, synthesis and evaluation of 3-methylene-substituted indolinones as antimalarials
  作者：S. Praveen Kumar、Jiri Gut、Rita C. Guedes、Philip J. Rosenthal、Maria M.M. Santos、Rui Moreira

  DOI：10.1016/j.ejmech.2011.01.008

  日期：2011.3

  The design, synthesis and evaluation of 3-methylene-substituted indolinones as falcipain inhibitors and antiplasmodial agents are described. These compounds react readily with thiols via an addition-elimination mechanism, indicating their potential as cysteine protease inhibitors. Several indolinones containing a Leu-i-amyl recognition moiety were found to be moderate inhibitors of the Plasmodium falciparum

  描述，设计和合成的3-亚甲基取代的吲哚啉酮作为falcipain抑制剂和抗疟原虫剂。这些化合物通过加成消除机制容易与硫醇反应，表明它们作为半胱氨酸蛋白酶抑制剂的潜力。含有具有Leu-几个吲哚满酮我发现戊识别部分是适度抑制剂的恶性疟原虫半胱氨酸蛋白酶falcipain-2，但不相关的蛋白酶falcipain-3，和针对抗氯喹显示抗疟原虫活性恶性疟原虫W2在低微摩尔范围内的应变。将7-氯喹啉部分偶联至3-亚甲基取代的吲哚酮骨架上导致抗血浆活性的显着改善。
• 1-Phenyl-2(1H,3H)-indolone psycho-therapeutic agents
  申请人：PFIZER INC.

  公开号：EP0104860A1

  公开（公告）日：1984-04-04

  Certain substituted 1-phenyl-3-(aminoalkylidene)-2(1H,3H)-indolones are highly potent gabaergic agents, valuable in the treatment of individuals suffering from schizophrenia or reversing the side effects of a previously or concurrently administered neuroleptic agent; or in the treatment of epilepsy. A wider class of substituted 1-phenyl-3-(aminoalkylidene)-2(1H,3H)-indolones, together with 1-phenyl-3-(2-pyrrolidinylidene)-2(1H,3H)-indolones, and homologs thereof, are valuable in the treatment of anxiety.

  某些取代的 1-苯基-3-(氨基亚烷基)-2(1H,3H)-吲哚酮是强效的伽巴能药物，对治疗精神分裂症患者或逆转之前或同时使用的神经安定剂的副作用，或治疗癫痫很有价值。还有一类取代的 1-苯基-3-(氨基亚烷基)-2(1H,3H)-吲哚酮，以及 1-苯基-3-(2-吡咯烷亚基)-2(1H,3H)-吲哚酮及其同系物，对治疗焦虑症很有价值。
• HOWARD, HARRY R.;SARGES, REINHARD
  作者：HOWARD, HARRY R.、SARGES, REINHARD

  DOI：——

  日期：——
• US4476307A
  申请人：——

  公开号：US4476307A

  公开（公告）日：1984-10-09
• US4861880A
  申请人：——

  公开号：US4861880A

  公开（公告）日：1989-08-29