2-(乙磺酰基)乙胺 | 173336-82-8

• 分子结构分类: 有机化合物 - 有机硫化合物 - 磺酰类
• 中文名称: 2-(乙磺酰基)乙胺
• 中文别名: [2-(乙基磺酰基)乙基]胺
• 英文名称: 2-ethanesulfonyl-ethylamine
• 英文别名: β-Amino-diaethylsulfon；β-Aethylsulfon-aethylamin；2-Aethansulfonyl-aethylamin；2-(Ethylsulfonyl)ethanamine；2-ethylsulfonylethanamine
• CAS: 173336-82-8
• 化学式: C₄H₁₁NO₂S
• mdl: MFCD11557713
• 分子量: 137.203
• InChiKey: JMCWLZFPCMLCBV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  68.5
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2921199090

反应信息

• 作为反应物：
  描述：

  (1S,3S,2'S,4'R)-[3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-1-(4'-methyl-5-oxo-tetrahydro-furan-2'-yl)-pentyl]-carbamic acid tert-butyl ester 、 2-(乙磺酰基)乙胺 生成 5(S)-tert-butoxycarbonylamino-4(S)-hydroxy-7(S)-isopropyl-2(R)-methyl-8-[4-methoxy-3-(3-methoxypropyloxy)-phenyl]-octanoic acid {N-[2-(ethylsulfonyl)-ethyl]} amide
  参考文献：
  名称：

  Novel 2,7-Dialkyl-Substituted 5(S)-Amino-4(S)-hydroxy-8-phenyl-octanecarboxamide Transition State Peptidomimetics Are Potent and Orally Active Inhibitors of Human Renin

  摘要：

  The action of renin is the rate-limiting step of the renin-angiotensin system (RAS), a key regulator of blood pressure. Effective renin inhibitors directly block the RAS entirely at source and, thus, may provide a vital weapon for hypertension therapy. Our efforts toward identifying novel small-molecule peptidomimetic renin inhibitors have resulted in the design of transition-state isosteres such as I bearing an all-carbon 8-phenyl-octanecarboxamide framework. Optimization of the extended P3 portion of I and extensive P2' modifications provided analogues with improved in vitro potencies in the presence of plasma. X-ray resolution of rhrenin/38a in the course of SAR work surprisingly unveiled the exploitation of a previously unexplored pocket (S3(SP)) important for strong binding affinities. Several inhibitors demonstrated oral efficacy in sodium-depleted marmosets. The most potent, 38a, induced dose-dependently a pronounced reduction in mean arterial blood pressure, paralleled by complete blockade of active plasma renin, up to 8 h post-dose. Oral bioavailability of 38a was 16% in marmosets.

  DOI：

  10.1021/jm070314y
• 作为产物：
  描述：

  2-(乙硫基)乙基胺盐酸盐 在 盐酸 、 potassium permanganate 作用下， 以 水 为溶剂， 反应 5.0h， 以96%的产率得到2-(乙磺酰基)乙胺
  参考文献：
  名称：

  Novel 2,7-Dialkyl-Substituted 5(S)-Amino-4(S)-hydroxy-8-phenyl-octanecarboxamide Transition State Peptidomimetics Are Potent and Orally Active Inhibitors of Human Renin

  摘要：

  The action of renin is the rate-limiting step of the renin-angiotensin system (RAS), a key regulator of blood pressure. Effective renin inhibitors directly block the RAS entirely at source and, thus, may provide a vital weapon for hypertension therapy. Our efforts toward identifying novel small-molecule peptidomimetic renin inhibitors have resulted in the design of transition-state isosteres such as I bearing an all-carbon 8-phenyl-octanecarboxamide framework. Optimization of the extended P3 portion of I and extensive P2' modifications provided analogues with improved in vitro potencies in the presence of plasma. X-ray resolution of rhrenin/38a in the course of SAR work surprisingly unveiled the exploitation of a previously unexplored pocket (S3(SP)) important for strong binding affinities. Several inhibitors demonstrated oral efficacy in sodium-depleted marmosets. The most potent, 38a, induced dose-dependently a pronounced reduction in mean arterial blood pressure, paralleled by complete blockade of active plasma renin, up to 8 h post-dose. Oral bioavailability of 38a was 16% in marmosets.

  DOI：

  10.1021/jm070314y

文献信息

• Toward Lead-Oriented Synthesis: One-Pot Version of Castagnoli Condensation with Nonactivated Alicyclic Anhydrides
  作者：Sergey V. Ryabukhin、Dmitriy M. Panov、Dmitry S. Granat、Eugeniy N. Ostapchuk、Dmitriy V. Kryvoruchko、Oleksandr O. Grygorenko

  DOI：10.1021/co4001277

  日期：2014.3.10

  One-pot variation of Castagnoli condensation, that is, reaction of cyclic anhydrides, amines, and aldehydes, has been developed as a combinatorial approach to 1,2-disubstituted 5-oxopyrrolidine- and 6-oxopiperidine-3-carboxylic acids, as well as their benzo-analogues. Utility of the method to multigram preparation of building blocks and synthetic intermediates was also demonstrated. The final products are obtained in high yields and diastereoselectivity. The method fits well in the concept of lead-oriented synthesis; in particular, it can be used for the design of lead-like Compound libraries, even if the strictest cut-offs are applied to the physicochemical properties of their members.
• Discovery and optimization of a highly efficacious class of 5-aryl-2-aminopyridines as FMS-like tyrosine kinase 3 (FLT3) inhibitors
  作者：Gang Liu、Sunny Abraham、Xing Liu、Shimin Xu、Allison M. Rooks、Ron Nepomuceno、Alan Dao、Daniel Brigham、Dana Gitnick、Darren E. Insko、Michael F. Gardner、Patrick P. Zarrinkar、Ron Christopher、Barbara Belli、Robert C. Armstrong、Mark W. Holladay

  DOI：10.1016/j.bmcl.2015.07.023

  日期：2015.9

  Based on a putative binding mode of quizartinib (AC220, 1), a potent FMS-like tyrosine kinase 3 (FLT3) inhibitor in Phase III clinical development, we have designed de novo a simpler aminopyridine-based hinge binding motif. Further optimization focusing on maximizing in vivo efficacy and minimizing CYP3A4 time-dependent inhibition resulted in a highly efficacious compound (6s) in tumor xenograft model for further preclinical development. (C) 2015 Elsevier Ltd. All rights reserved.
• Grot,C. et al., Justus Liebigs Annalen der Chemie, 1964, vol. 679, p. 42 - 50
  作者：Grot,C. et al.

  DOI：——

  日期：——
• SAR studies on a novel series of human cytomegalovirus primase inhibitors
  作者：X. Chen、J. Adrian、T. Cushing、H. DiMaio、L. Liang、V. Mayorga、S. Miao、M.G. Peterson、J.P. Powers、F. Spector、C. Stein、M. Wright、D. Xu、Q. Ye、J. Jaen

  DOI：10.1016/j.bmcl.2007.01.109

  日期：2007.4

  A novel series of imidazolylpyrimidines were found to possess inhibitory activity against the human CMV UL70 primase. Extensive SAR studies on an HTS lead led to potent, orally bioavailable compounds with anti-CMV IC50 values of 150 nM in both viral yield and viral DNA replication assays and with a much reduced cytotoxicity compared to marketed treatments ganciclovir and cidofovir. (c) 2007 Elsevier Ltd. All rights reserved.