4-((tert-butoxycarbonyl)amino)benzyl methanesulfonate | 252919-04-3

• 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: 4-((tert-butoxycarbonyl)amino)benzyl methanesulfonate
• 英文别名: N-[4-[[(methylsulfonyl)oxy]methyl]phenyl]carbamic acid 1,1-dimethylethyl ester；[4-[(2-methylpropan-2-yl)oxycarbonylamino]phenyl]methyl methanesulfonate
• CAS: 252919-04-3
• 化学式: C₁₃H₁₉NO₅S
• 分子量: 301.364
• InChiKey: XPTNUILTVANCMN-UHFFFAOYSA-N

物化性质

• 沸点：
  421.1±38.0 °C(Predicted)
• 密度：
  1.262±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  90.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-((tert-butoxycarbonyl)amino)benzyl methanesulfonate 在 盐酸 、 potassium carbonate 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  Rational design, synthesis and structure–Activity relationships of a cyclic succinate series of TNF-α converting enzyme inhibitors. Part 1: lead identification

  摘要：

  Rational design based on the broad spectrum MMP inhibitor CGS 27023A led to the identification of a novel series of cyclic succinate TACE inhibitors. As a mixture of two enantiomers, the lead compound 17b exhibited potent enzyme activity (IC50 = 8 nM) in the inhibition of porcine TNF-alpha converting enzyme (pTACE) and excellent selectivity over aggrecanase and MMP-1, -2 and -9. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.09.056
• 作为产物：
  描述：

  对氨基苯甲醇 在 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 4-((tert-butoxycarbonyl)amino)benzyl methanesulfonate
  参考文献：
  名称：

  Rational design, synthesis and structure–Activity relationships of a cyclic succinate series of TNF-α converting enzyme inhibitors. Part 1: lead identification

  摘要：

  Rational design based on the broad spectrum MMP inhibitor CGS 27023A led to the identification of a novel series of cyclic succinate TACE inhibitors. As a mixture of two enantiomers, the lead compound 17b exhibited potent enzyme activity (IC50 = 8 nM) in the inhibition of porcine TNF-alpha converting enzyme (pTACE) and excellent selectivity over aggrecanase and MMP-1, -2 and -9. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.09.056

文献信息

• Chemokine receptor binding heterocyclic compounds
  申请人：——

  公开号：US20030028022A1

  公开（公告）日：2003-02-06

  Compounds which modulate chemokine receptor activities are disclosed. These compounds are preferably tertiary amines comprising tetrahydroquinoline and benzimidazole.

  本发明揭示了调节趋化因子受体活性的化合物。这些化合物通常为包含四氢喹啉和苯并咪唑的三级胺。
• WO2008/34124
  申请人：——

  公开号：——

  公开（公告）日：——
• Studies of CDK 8/19 inhibitors: Discovery of novel and selective CDK8/19 dual inhibitors and elimination of their CYP3A4 time-dependent inhibition potential
  作者：Jun Fujimoto、Takaharu Hirayama、Yasuhiro Hirata、Yukiko Hikichi、Saomi Murai、Maki Hasegawa、Yuka Hasegawa、Kazuko Yonemori、Akito Hata、Kazunobu Aoyama、Douglas R. Cary

  DOI：10.1016/j.bmc.2017.03.049

  日期：2017.6

  In this article, synthetic studies around a pyridylacrylamide-based hit compound (1), utilizing structure based drug design guided by CDK8 docking models, is discussed. Modification of the pendant 4-fluorophenyl group to various heteroaromatic rings was conducted aiming an interaction with the proximal amino acids, and then replacement of the morpholine ring was targeted for decreasing potential of time dependent CYP3A4 inhibition. These efforts led to the compound 4k, with enhanced CDK8 inhibitory activity and no apparent potential for time-dependent CYP3A4 inhibition (CDK8 IC50: 2.5 nM; CYP3A4 TDI: 99% compound remaining). Compound 4k was found to possess a highly selective kinase inhibition profile, and also showed favorable pharmacokinetic profile. Oral administration of 4k (15 mg/kg, bid. for 2 weeks) suppressed tumor growth (TIC 29%) in an RPM18226 mouse xenograft model. (C) 2017 Elsevier Ltd. All rights reserved.
• CHEMOKINE RECEPTOR BINDING HETEROCYCLIC COMPOUNDS
  申请人：ANORMED INC.

  公开号：EP1317451A1

  公开（公告）日：2003-06-11
• Methods for Identifying Compounds that Modulate Enzymatic Activities by Employing Covalently Bonded Target-Extender Complexes with Ligand Candidates
  申请人：Erianson Daniel A.

  公开号：US20080220536A1

  公开（公告）日：2008-09-11

  The present invention relates to the use of “tethering” to identify compounds that modulate enzymatic activity.