benzyl N-(2-amino-2-sulfanylideneethyl)-N-ethylcarbamate | 115173-00-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: benzyl N-(2-amino-2-sulfanylideneethyl)-N-ethylcarbamate
• CAS: 115173-00-7
• 化学式: C₁₂H₁₆N₂O₂S
• 分子量: 252.337
• InChiKey: HJHSTPMUUWSYPU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  87.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  benzyl N-(2-amino-2-sulfanylideneethyl)-N-ethylcarbamate 在 氢溴酸 、 溶剂黄146 作用下， 反应 0.33h， 以1.3 g的产率得到2-(Ethylamino)ethanethioamide
  参考文献：
  名称：

  Core Refinement toward Permeable β-Secretase (BACE-1) Inhibitors with Low hERG Activity

  摘要：

  By use of iterative design aided by predictive models for target affinity, brain permeability, and hERG activity, novel and diverse compounds based on cyclic amidine and guanidine cores were synthesized with the goal of finding BACE-1 inhibitors as a treatment for Alzheimer's disease. Since synthesis feasibility had low priority in the design of the cores, an extensive synthesis effort was needed to make the relevant compounds. Syntheses of these compounds are reported, together with physicochemical properties and structure-activity relationships based on in vitro data. Four crystal structures of diverse amidines binding in the active site are deposited and discussed. Inhibitors of BACE-1 with 3 mu M to 32 nM potencies in cells are shown, together with data on in vivo brain exposure levels for four compounds. The results presented show the importance of the core structure for the profile of the final compounds.

  DOI：

  10.1021/jm3011349
• 作为产物：
  描述：

  N-苄氧羰基氨基乙腈 在 硫化氢 、 sodium hydride 、 三乙胺 作用下， 以 吡啶 为溶剂， 反应 18.0h， 生成 benzyl N-(2-amino-2-sulfanylideneethyl)-N-ethylcarbamate
  参考文献：
  名称：

  新的7-取代的喹诺酮类抗菌剂。1-乙基-1,4-二氢-4-氧代-7-（2-噻唑基和4-噻唑基）-3-喹啉羧酸的合成

  摘要：

  一系列1-乙基-1,4-二氢-4-氧代-7-（4-噻唑基）-3-喹啉羧酸和1-乙基-1,4-二氢-4-氧代-7-（2-噻唑基制备）-3-喹啉羧酸。还制备了10- [2-（氨基甲基）-4-噻唑基] -9-氟-2,3-二氢-3-甲基-7-氧代-7 H-吡啶基[1,2,3- de ] [1 ，4]苯并恶嗪-6-羧酸。发现在噻唑部分具有碱性胺取代基的类似物具有抗菌活性。

  DOI：

  10.1002/jhet.5570240604

文献信息

• CULBERTSON, TOWNLEY P.;DOMAGALA, JOHN M.;PETERSON, PHRED;BONGERS, SHANNON+, J. HETEROCYCL. CHEM., 24,(1987) N 6, 1509-1520
  作者：CULBERTSON, TOWNLEY P.、DOMAGALA, JOHN M.、PETERSON, PHRED、BONGERS, SHANNON+

  DOI：——

  日期：——
• Core Refinement toward Permeable β-Secretase (BACE-1) Inhibitors with Low hERG Activity
  作者：Tobias Ginman、Jenny Viklund、Jonas Malmström、Jan Blid、Rikard Emond、Rickard Forsblom、Anh Johansson、Annika Kers、Fredrik Lake、Fernando Sehgelmeble、Karin J. Sterky、Margareta Bergh、Anders Lindgren、Patrik Johansson、Fredrik Jeppsson、Johanna Fälting、Ylva Gravenfors、Fredrik Rahm

  DOI：10.1021/jm3011349

  日期：2013.6.13

  By use of iterative design aided by predictive models for target affinity, brain permeability, and hERG activity, novel and diverse compounds based on cyclic amidine and guanidine cores were synthesized with the goal of finding BACE-1 inhibitors as a treatment for Alzheimer's disease. Since synthesis feasibility had low priority in the design of the cores, an extensive synthesis effort was needed to make the relevant compounds. Syntheses of these compounds are reported, together with physicochemical properties and structure-activity relationships based on in vitro data. Four crystal structures of diverse amidines binding in the active site are deposited and discussed. Inhibitors of BACE-1 with 3 mu M to 32 nM potencies in cells are shown, together with data on in vivo brain exposure levels for four compounds. The results presented show the importance of the core structure for the profile of the final compounds.
• New 7-substituted quinolone antibacterial agents. The synthesis of 1-ethyl-1,4-dihydro-4-oxo-7-(2-thiazolyl and 4-thiazolyl)-3-quinolinecarboxylic acids
  作者：Townley P. Culbertson、John M. Domagala、Phred Peterson、Shannon Bongers、Jeffrey B. Nichols

  DOI：10.1002/jhet.5570240604

  日期：1987.11

  4-dihydro-4-oxo-7-(4-thiazolyl)-3-quinolinecarboxylic acids and 1-ethyl-1,4-dihydro-4-oxo-7-(2-thiazolyl)-3-quinolinecarboxylic acids were prepared. Also prepared was 10-[2-(aminomethyl)-4-thiazolyl]-9-fluoro-2,3-dihydro-3-methyl-7-oxo-7H-pyrido[1,2,3-de][1,4]benzoxazine-6-carboxylic acid. Analogs with basic amine substituents on the thiazole moiety were found to have antibacterial activity.

  一系列1-乙基-1,4-二氢-4-氧代-7-（4-噻唑基）-3-喹啉羧酸和1-乙基-1,4-二氢-4-氧代-7-（2-噻唑基制备）-3-喹啉羧酸。还制备了10- [2-（氨基甲基）-4-噻唑基] -9-氟-2,3-二氢-3-甲基-7-氧代-7 H-吡啶基[1,2,3- de ] [1 ，4]苯并恶嗪-6-羧酸。发现在噻唑部分具有碱性胺取代基的类似物具有抗菌活性。