1-乙酰基-5-(氯乙酰基)二氢吲哚 | 76139-03-2

• 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: 1-乙酰基-5-(氯乙酰基)二氢吲哚
• 英文名称: acetyl-1 chloroacetyl-5 indoline
• 英文别名: Ethanone, 1-(1-acetyl-2,3-dihydro-1H-indol-5-yl)-2-chloro-；1-(1-acetyl-2,3-dihydroindol-5-yl)-2-chloroethanone
• CAS: 76139-03-2
• 化学式: C₁₂H₁₂ClNO₂
• mdl: MFCD02934406
• 分子量: 237.686
• InChiKey: CBLHPICDDMRZIW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-乙酰基-5-(氯乙酰基)二氢吲哚 在 palladium on activated charcoal 吡啶 、 盐酸 、 potassium cyanide 、 manganese(IV) oxide 、 sodium hydroxide 、 sodium tetrahydroborate 、 tetrafluoroboric acid 、 双氧水 、 硝酸 、 溶剂黄146 、 锌 、 sodium nitrite 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 溶剂黄146 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， -5.0~60.0 ℃ 、101.33 kPa 条件下， 反应 26.58h， 生成 5-(1-羟基-2-氨基乙基)-1H-吲哚-7-甲酰胺
  参考文献：
  名称：

  Indole-phenol-bioisosterism. Synthesis and antihypertensive activity of a pyrrolo analog of labetalol

  摘要：

  The synthesis of 5-[hydroxy-2-[(1-methyl-3-phenylpropyl)amino]ethyl]-1H-indole-7- carboxamide, 5, a pyrrolo analogue of labetalol, is described. Compound 5 was found to reduce blood pressure in spontaneously hypertensive rats with an ED50 of 5 mg/kg po, without causing any decrease in heart rate. Isolated tissue studies with 5 shows that it is a nonselective beta-adrenoceptor antagonist and that it is a weaker alpha-adrenoceptor antagonist with a relative selectivity for alpha 1-receptors. Additionally, the compound displayed significant beta-adrenoceptor intrinsic sympathomimetic activity. Evidence is presented that the beta-adrenoceptor antagonist and agonist properties of 5 are mediated via hydrogen-bond formation with the receptor.

  DOI：

  10.1021/jm00156a019
• 作为产物：
  描述：

  N-乙酰基吲哚啉 、 氯乙酰氯 在 三氯化铝 作用下， 生成 1-乙酰基-5-(氯乙酰基)二氢吲哚
  参考文献：
  名称：

  Indole-phenol-bioisosterism. Synthesis and antihypertensive activity of a pyrrolo analog of labetalol

  摘要：

  The synthesis of 5-[hydroxy-2-[(1-methyl-3-phenylpropyl)amino]ethyl]-1H-indole-7- carboxamide, 5, a pyrrolo analogue of labetalol, is described. Compound 5 was found to reduce blood pressure in spontaneously hypertensive rats with an ED50 of 5 mg/kg po, without causing any decrease in heart rate. Isolated tissue studies with 5 shows that it is a nonselective beta-adrenoceptor antagonist and that it is a weaker alpha-adrenoceptor antagonist with a relative selectivity for alpha 1-receptors. Additionally, the compound displayed significant beta-adrenoceptor intrinsic sympathomimetic activity. Evidence is presented that the beta-adrenoceptor antagonist and agonist properties of 5 are mediated via hydrogen-bond formation with the receptor.

  DOI：

  10.1021/jm00156a019

文献信息

• [EN] N-SUBSTITUTED PIPERIDINE AND PIPERAZINE DERIVATIVES<br/>[FR] DERIVES DE PIPERIDINE ET DE PIPERAZINE N-SUBSTITUES
  申请人：WARNER LAMBERT CO

  公开号：WO2005066165A1

  公开（公告）日：2005-07-21

  This invention relates to compounds of the formula 1 wherein R1, R2, R7, R8, R9, U, V, Z, A, W, X, M, E, L, T and D are defined as in the specification, pharmaceutical compositions containing them and their use in the treatment of central nervous system and other disorders.

  这项发明涉及式1的化合物，其中R1、R2、R7、R8、R9、U、V、Z、A、W、X、M、E、L、T和D的定义如规范中所述，包含它们的药物组合物以及它们在治疗中枢神经系统和其他疾病中的用途。
• Recyclization of 9-bromocotarnine under the action of haloacylhetarenes. Synthesis and biological activity of the 4-heteroaroyl-9-bromo-1,2-dihydro-6-methoxy-7,8-methylenedioxy-3-benzazepines
  作者：A. A. Zubenko、L. N. Divaeva、A. S. Morkovnik、V. G. Kartsev、Y. D. Drobin、N. M. Serbinovskaya、L. N. Fetisov、A. N. Bodryakov、M. A. Bodryakova、L. A. Lyashenko、A. I. Klimenko

  DOI：10.1134/s1068162017040173

  日期：2017.9

  ines. It has been shown that some of the resulting compounds exhibit a significant antibacterial activity against Staphylococcus aureus and Escherichia coli. At the same time, the synthesized benzazepines have shown no significant protistocidal activity against Colpoda steinii and fungistatic activity against Penicillium italicum.

  9-bromocotarnine 与杂环 α-卤代酮的反应伴随着六元二氢吡啶环扩展为七元二氢氮杂环并导致以前未知的 4-heteroaroyl-9-bromo-3-methyl-1,2-二氢-6-甲氧基-7,8-亚甲二氧基-3-苯并氮杂。已经表明，一些所得化合物对金黄色葡萄球菌和大肠杆菌表现出显着的抗菌活性。同时，合成的苯并氮杂没有显示出显着的对青霉的杀原生生物活性和对意大利青霉的抑菌活性。
• Vallat; Grossi; Boucherle, European Journal of Medicinal Chemistry, 1981, vol. 16, # 5, p. 409 - 414
  作者：Vallat、Grossi、Boucherle、Simiand

  DOI：——

  日期：——
• Terent'ew et al., Zhurnal Obshchei Khimii, 1959, vol. 29, p. 2875,2880; engl. Ausg. S. 2835, 2840
  作者：Terent'ew et al.

  DOI：——

  日期：——
• Grossi, Pierre-Jean; Vallat, Jean-Noel; Boucherle, Andre, European Journal of Medicinal Chemistry, 1980, vol. 15, # 3, p. 285 - 298
  作者：Grossi, Pierre-Jean、Vallat, Jean-Noel、Boucherle, Andre、Simiand, Jacques

  DOI：——

  日期：——