4-氨基-d-苯基丙氨酸甲酯 | 150570-99-3

• 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
• 中文名称: 4-氨基-d-苯基丙氨酸甲酯
• 英文名称: 4-Amino-D-phenylalanine methyl ester
• 英文别名: methyl (2R)-2-amino-3-(4-aminophenyl)propanoate
• CAS: 150570-99-3
• 化学式: C₁₀H₁₄N₂O₂
• 分子量: 194.233
• InChiKey: VWHHEDIHZWZRTF-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  78.3
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-氨基-d-苯基丙氨酸甲酯 、 N,N'-羰基二咪唑 以 四氢呋喃 为溶剂， 生成
  参考文献：
  名称：

  The synthesis and SAR of calcitonin gene-related peptide (CGRP) receptor antagonists derived from tyrosine surrogates. Part 1

  摘要：

  We have systematically studied the effects of varying the central unnatural amino acid moiety on CGRP receptor antagonist potency and CYP inhibition in a series of ureidoamides. In this Letter, we report the discovery of compound 23, a potent CGRP receptor antagonist with only weak CYP3A4 inhibition. Unlike the triptans, compound 23 did not cause active constriction of ex vivo human cerebral arteries. At doses of 0.3-1 mg/kg (sc), 23 showed robust inhibition of CGRP-induced increases in marmoset facial blood flow, a validated migraine model. Ureidoamide 23 derives from a novel amino acid, 1H-indazol-5-yl substituted alanine as a tyrosine surrogate. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.05.074
• 作为产物：
  描述：

  methyl p-amino-DL-phenylalaninate dihydrochloride 在 碳酸氢铵 、 水 作用下， 以 二氯甲烷 为溶剂， 反应 26.0h， 生成 4-氨基-L-苯丙氨酸 、 4-氨基-d-苯基丙氨酸甲酯
  参考文献：
  名称：

  Ricca, Jean-Marc; Crout, David H. G., Journal of the Chemical Society. Perkin transactions I, 1993, # 11, p. 1225 - 1234

  摘要：

  DOI：

文献信息

• Ricca, Jean-Marc; Crout, David H. G., Journal of the Chemical Society. Perkin transactions I, 1993, # 11, p. 1225 - 1234
  作者：Ricca, Jean-Marc、Crout, David H. G.

  DOI：——

  日期：——
• The synthesis and SAR of calcitonin gene-related peptide (CGRP) receptor antagonists derived from tyrosine surrogates. Part 1
  作者：Xiaojun Han、Rita L. Civiello、Charles M. Conway、Deborah A. Cook、Carl D. Davis、Robert Macci、Sokhom S. Pin、Shelly X. Ren、Richard Schartman、Laura J. Signor、George Thalody、Kimberly A. Widmann、Cen Xu、Prasad V. Chaturvedula、John E. Macor、Gene M. Dubowchik

  DOI：10.1016/j.bmcl.2012.05.074

  日期：2012.7

  We have systematically studied the effects of varying the central unnatural amino acid moiety on CGRP receptor antagonist potency and CYP inhibition in a series of ureidoamides. In this Letter, we report the discovery of compound 23, a potent CGRP receptor antagonist with only weak CYP3A4 inhibition. Unlike the triptans, compound 23 did not cause active constriction of ex vivo human cerebral arteries. At doses of 0.3-1 mg/kg (sc), 23 showed robust inhibition of CGRP-induced increases in marmoset facial blood flow, a validated migraine model. Ureidoamide 23 derives from a novel amino acid, 1H-indazol-5-yl substituted alanine as a tyrosine surrogate. (C) 2012 Elsevier Ltd. All rights reserved.