2-(2-Methoxyphenylmercapto)aethylamin | 67215-18-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(2-Methoxyphenylmercapto)aethylamin
• 英文别名: 2-[(2-methoxyphenyl)thio]ethanamine；2-(2-methoxyphenylthio)-ethylamine；2-(2-Methoxy-phenylsulfanyl)-ethylamine；2-(2-methoxyphenyl)sulfanylethanamine
• CAS: 67215-18-3
• 化学式: C₉H₁₃NOS
• 分子量: 183.274
• InChiKey: FWTYMSQXRXREFR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  60.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(2-Methoxyphenylmercapto)aethylamin 、 4-环氧丙烷氧基咔唑 以 异丙醇 为溶剂， 反应 2.0h， 以69%的产率得到1-(9H-carbazol-4-yloxy)-3-[[2-(2-methoxyphenylthio)-ethyl]amino]-2-propanol
  参考文献：
  名称：

  Novel Carvedilol Analogues That Suppress Store-Overload-Induced Ca²⁺ Release

  摘要：

  Carvedilol is a uniquely effective drug for the treatment of cardiac arrhythmias in patients with heart failure. This activity is in part because of its ability to inhibit store-overload-induced calcium release (SOICR) through the RyR2 channel. We describe the synthesis, characterization, and bioassay of ca. 100 compounds based on the carvedilol motif to identify features that correlate with and optimize SOICR inhibition. A single-cell bioassay was employed on the basis of the RyR2-R4496C mutant HEK-293 cell line in which calcium release from the endoplasmic reticulum through the defective channel was measured. IC50 values for SOICR inhibition were thus obtained. The compounds investigated contained modifications to the three principal subunits of carvedilol, including the carbazole and catechol moieties, as well as the linker chain containing the beta-amino alcohol functionality. The SAR results indicate that significant alterations are tolerated in each of the three subunits.

  DOI：

  10.1021/jm401090a
• 作为产物：
  描述：

  2-{2-[(2-methoxyphenyl)thio]ethyl}-1H-isoindole-1,3(2H)-dione 在 一水合肼 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以76%的产率得到2-(2-Methoxyphenylmercapto)aethylamin
  参考文献：
  名称：

  Design, synthesis, and pharmacological effects of structurally simple ligands for MT1 and MT2 melatonin receptors

  摘要：

  A series of phenoxyalkyl and phenylthioalkyl amides were prepared as melatoninergic ligands. Modulation of affinity of the newly synthesized compound by applying SARs around the terminal amide moiety, the alkyl chain, and the methoxy group on the aromatic ring provides compounds with nanomolar affinity for both melatonin receptor subtypes. Affinity towards MT1 and MT2 receptors were modulated also exploiting chirality. The investigation of intrinsic activity revealed that all the tested compounds behave as full or partial agonists. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.06.100

文献信息

• Carbazolyl-(4)-oxypropanolamine compounds and therapeutic compositions
  申请人：Boehringer Mannheim GmbH

  公开号：US04503067A1

  公开（公告）日：1985-03-05

  Carbazolyl-(4)-oxypropanolamine compounds of the formula ##STR1## wherein R.sub.1 is hydrogen, lower alkanoyl or aroyl; R.sub.2 is hydrogen, lower alkyl or arylalkyl; R.sub.3 is hydrogen or lower alkyl; R.sub.4 is hydrogen or lower alkyl, or when X is oxygen, R.sub.4 together with R.sub.5 can represent --CH.sub.2 --O--; X is a valency bond, --CH.sub.2 --, oxygen or sulfur; Ar is mono- or bicyclic aryl or pyridyl; R.sub.5 and R.sub.6 are individually selected from hydrogen, halogen, hydroxyl, lower alkyl, aminocarbonyl, lower alkoxy, aralkyloxy, lower alkylthio, lower alkylsulphinyl or lower alkylsulphonyl; R.sub.5 and R.sub.6 together can represent methylenedioxy; and the salts thereof with physiologically acceptable acids are outstandingly effective in the treatment and prophylaxis of circulatory and cardiac diseases, e.g., hypertension and angina pectoris.

  Carbazolyl-(4)-oxypropanolamine化合物的化学式为##STR1##其中R.sub.1是氢，较低的烷酰基或芳酰基；R.sub.2是氢，较低的烷基或芳基烷基；R.sub.3是氢或较低的烷基；R.sub.4是氢或较低的烷基，或者当X是氧时，R.sub.4与R.sub.5一起可以代表--CH.sub.2--O--；X是一个价键，--CH.sub.2--，氧或硫；Ar是单环或双环芳基或吡啶基；R.sub.5和R.sub.6分别选自氢，卤素，羟基，较低的烷基，氨基甲酰基，较低的烷氧基，芳基烷氧基，较低的烷基硫基，较低的烷基磺基；R.sub.5和R.sub.6一起可以代表亚甲二氧基；以及它们与生理上可接受的酸盐在治疗和预防循环和心脏疾病，例如高血压和心绞痛方面具有卓越的疗效。
• Carbazolyl-(4)-oxy-propanolamin-Derivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel
  申请人：BOEHRINGER MANNHEIM GMBH

  公开号：EP0004920B1

  公开（公告）日：1981-08-05
• US4503067A
  申请人：——

  公开号：US4503067A

  公开（公告）日：1985-03-05
• Design, synthesis, and pharmacological effects of structurally simple ligands for MT1 and MT2 melatonin receptors
  作者：Alessia Carocci、Alessia Catalano、Angelo Lovece、Giovanni Lentini、Andrea Duranti、Valeria Lucini、Marilou Pannacci、Francesco Scaglione、Carlo Franchini

  DOI：10.1016/j.bmc.2010.06.100

  日期：2010.9

  A series of phenoxyalkyl and phenylthioalkyl amides were prepared as melatoninergic ligands. Modulation of affinity of the newly synthesized compound by applying SARs around the terminal amide moiety, the alkyl chain, and the methoxy group on the aromatic ring provides compounds with nanomolar affinity for both melatonin receptor subtypes. Affinity towards MT1 and MT2 receptors were modulated also exploiting chirality. The investigation of intrinsic activity revealed that all the tested compounds behave as full or partial agonists. (C) 2010 Elsevier Ltd. All rights reserved.
• Novel Carvedilol Analogues That Suppress Store-Overload-Induced Ca²⁺ Release
  作者：Chris D. Smith、Aixia Wang、Kannan Vembaiyan、Jingqun Zhang、Cuihong Xie、Qiang Zhou、Guogen Wu、S. R. Wayne Chen、Thomas G. Back

  DOI：10.1021/jm401090a

  日期：2013.11.14

  Carvedilol is a uniquely effective drug for the treatment of cardiac arrhythmias in patients with heart failure. This activity is in part because of its ability to inhibit store-overload-induced calcium release (SOICR) through the RyR2 channel. We describe the synthesis, characterization, and bioassay of ca. 100 compounds based on the carvedilol motif to identify features that correlate with and optimize SOICR inhibition. A single-cell bioassay was employed on the basis of the RyR2-R4496C mutant HEK-293 cell line in which calcium release from the endoplasmic reticulum through the defective channel was measured. IC50 values for SOICR inhibition were thus obtained. The compounds investigated contained modifications to the three principal subunits of carvedilol, including the carbazole and catechol moieties, as well as the linker chain containing the beta-amino alcohol functionality. The SAR results indicate that significant alterations are tolerated in each of the three subunits.