(R)-2-tert-Butoxycarbonylamino-6-(2-chloro-benzyloxycarbonylamino)-hexanoic acid methyl ester | 78444-81-2

• 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-6-(2-chloro-benzyloxycarbonylamino)-hexanoic acid methyl ester
• CAS: 78444-81-2
• 化学式: C₂₀H₂₉ClN₂O₆
• 分子量: 428.913
• InChiKey: OVYIDCNJKRGIGF-MRXNPFEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  29.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  102.96
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (R)-2-tert-Butoxycarbonylamino-6-(2-chloro-benzyloxycarbonylamino)-hexanoic acid methyl ester 在 吡啶 、 4-二甲氨基吡啶 、 二甲基硫 、 二异丁基氢化铝 、 臭氧 、 N,N-二异丙基乙胺 、 lithium chloride 、 zinc(II) chloride 作用下， 生成 tert-butyl (E,4R,5R)-4-acetyloxy-9-[(2-chlorophenyl)methoxycarbonylamino]-5-[(2-methylpropan-2-yl)oxycarbonylamino]non-2-enoate
  参考文献：
  名称：

  Synthesis and evaluation of pseudopeptide analogues of a specific CXCR4 inhibitor, T140: The insertion of an (E)-alkene dipeptide isostere into the βII′-turn moiety

  摘要：

  A 14-residue peptide, T140, strongly inhibits the T-cell line-tropic HIV-1 (X4-HIV-1) infection, since this peptide functions as a specific antagonist against a chemokine receptor, CXCR4. T140 takes an antiparallel beta-sheet structure with a type II' P-turn. In the present paper, we have designed and synthesized several T140 analogues in which an (E)-alkene dipeptide isostere was inserted into the type II' beta-turn moiety, as a bridging study to develop nonpeptidic CXCR4 inhibitors. It has been proven that the turn region of T140 can be replaced by the above surrogate with the maintenance of strong anti-HIV activity. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00041-0
• 作为产物：
  描述：

  Boc-N'-(2-氯苄氧羰基)-D-赖氨酸 、 碘甲烷 在 potassium hydrogencarbonate 作用下， 以100%的产率得到(R)-2-tert-Butoxycarbonylamino-6-(2-chloro-benzyloxycarbonylamino)-hexanoic acid methyl ester
  参考文献：
  名称：

  Synthesis and evaluation of pseudopeptide analogues of a specific CXCR4 inhibitor, T140: The insertion of an (E)-alkene dipeptide isostere into the βII′-turn moiety

  摘要：

  A 14-residue peptide, T140, strongly inhibits the T-cell line-tropic HIV-1 (X4-HIV-1) infection, since this peptide functions as a specific antagonist against a chemokine receptor, CXCR4. T140 takes an antiparallel beta-sheet structure with a type II' P-turn. In the present paper, we have designed and synthesized several T140 analogues in which an (E)-alkene dipeptide isostere was inserted into the type II' beta-turn moiety, as a bridging study to develop nonpeptidic CXCR4 inhibitors. It has been proven that the turn region of T140 can be replaced by the above surrogate with the maintenance of strong anti-HIV activity. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00041-0