(R)-2-tert-butoxycarbonylamino-3-(4-fluorobenzyloxy)propionic acid | 616894-98-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (R)-2-tert-butoxycarbonylamino-3-(4-fluorobenzyloxy)propionic acid
• 英文别名: tert-butyl N-[(2R)-1-[[5-(4-chlorophenyl)-3,3-dimethyl-1,1-dioxo-2H-1,2-thiazol-4-yl]methyl-ethylamino]-1-oxo-3-phenylmethoxypropan-2-yl]carbamate
• CAS: 616894-98-5
• 化学式: C₂₉H₃₈ClN₃O₆S
• 分子量: 592.156
• InChiKey: BGNSQJKNWALBAE-XMMPIXPASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  40
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  122
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (R)-2-tert-butoxycarbonylamino-3-(4-fluorobenzyloxy)propionic acid 在 盐酸 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 乙醇 、 二氯甲烷 、 醋酸异丙酯 、 水 为溶剂， 生成 2-(R)-2-(2-amino-2-methylpropionylamino)-3-phenylmethoxypropionic acid N-(5-(4-chlorophenyl)-3,3-dimethyl-1,1-dioxo-2,3-dihydroisothiazol-4-ylmethyl)-N-ethylamide hydrochloride
  参考文献：
  名称：

  Structure activity studies of the serine-AIB dipeptide domain in 2,3-dihydroisothiazole based growth hormone secretagogues

  摘要：

  A series of growth hormone secretagogues (GHSs) based on 2,3-dihydroisothiazole has been synthesized in the search for a potential treatment of growth hormone deficiency or frailty in the elderly. This paper describes the evaluation of the SAR of the benzyl-D-Ser-aminoisobutyric acid dipeptide fragment. Introduction of substituents in the peptide backbone and in the phenyl ring has been investigated, as well as replacements for the benzyl group and for the AIB residue. A number of modifications resulted in enhanced potency over the parent benzyl-D-Ser-AIB derivative. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.07.070
• 作为产物：
  描述：

  [5-(4-chlorophenyl)-3,3-dimethyl-1,1-dioxo-2,3-dihydroisothiazol-4-ylmethyl]ethylamine 、 N-Boc-O-苄基-D-丝氨酸 在 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 IPAc 、 水 为溶剂， 反应 14.0h， 以55%的产率得到(R)-2-tert-butoxycarbonylamino-3-(4-fluorobenzyloxy)propionic acid
  参考文献：
  名称：

  [EN] DIPEPTIDIC GROWTH HORMONE SECRETAGOGUES
  [FR] SECRETAGOGUES D'HORMONE DE CROISSANCE

  摘要：

  公开号：

  WO2003087069A3

文献信息

• [EN] DIPEPTIDIC GROWTH HORMONE SECRETAGOGUES<br/>[FR] SECRETAGOGUES D'HORMONE DE CROISSANCE
  申请人：——

  公开号：WO2003087069A3

  公开（公告）日：2004-03-25
• Structure activity studies of the serine-AIB dipeptide domain in 2,3-dihydroisothiazole based growth hormone secretagogues
  作者：Britta Evers、Gerd Ruehter、Martina Berg、Jeffrey A. Dodge、Dirk Hankotius、Ulrike Hary、Louis N. Jungheim、Hans-Juergen Mest、Eva-Maria Martin de la Nava、Michael Mohr、Brian S. Muehl、Soenke Petersen、Birgit Sommer、Grit Riedel-Herold、Mark J. Tebbe、Kenneth J. Thrasher、Silke Voelkers

  DOI：10.1016/j.bmc.2005.07.070

  日期：2005.12

  A series of growth hormone secretagogues (GHSs) based on 2,3-dihydroisothiazole has been synthesized in the search for a potential treatment of growth hormone deficiency or frailty in the elderly. This paper describes the evaluation of the SAR of the benzyl-D-Ser-aminoisobutyric acid dipeptide fragment. Introduction of substituents in the peptide backbone and in the phenyl ring has been investigated, as well as replacements for the benzyl group and for the AIB residue. A number of modifications resulted in enhanced potency over the parent benzyl-D-Ser-AIB derivative. (c) 2005 Elsevier Ltd. All rights reserved.