tert-butyl L-2-(tert-butoxycarbonyl)amino-4-(thioureidooxy)-butyrate | 364790-10-3

• 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
• 英文名称: tert-butyl L-2-(tert-butoxycarbonyl)amino-4-(thioureidooxy)-butyrate
• 英文别名: tert-butyl (2S)-4-(carbamothioylamino)oxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoate
• CAS: 364790-10-3
• 化学式: C₁₄H₂₇N₃O₅S
• 分子量: 349.451
• InChiKey: OZPJBMBCDJXNBF-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  23
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  144
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tert-butyl L-2-(tert-butoxycarbonyl)amino-4-(thioureidooxy)-butyrate 在 盐酸 、 碳酸氢钠 作用下， 以 1,4-二氧六环 、 乙腈 为溶剂， 反应 4.0h， 生成 L-2-amino-4-(S-methylthiothioureidooxy)butanoic acid hydrochloride
  参考文献：
  名称：

  Preparation and evaluation of new l-canavanine derivatives as nitric oxide synthase inhibitors

  摘要：

  New derivatives of the amino acid L-canavanine were prepared by total chemical synthesis and evaluated as inhibitors of inducible nitric oxide synthase (NOS). Replacement of the delta -methylene group of known NOS inhibitors with an oxygen atom produced dramatic effects as to the ability of these compounds to interact with the enzyme. These results indicate that the addition of an electron withdrawing group in the side chain of L-arginine-derived NOS inhibitors must be considered during inhibitor design depending on the expected mode of interaction with the enzyme. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00547-6
• 作为产物：
  描述：

  Boc-L-天冬氨酸 4-苄酯 在 palladium on activated charcoal 哌啶 、 4-二甲氨基吡啶 、 硼烷四氢呋喃络合物 、 氢气 、 N,N'-二环己基碳二亚胺 、 三苯基膦 、 肼 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 为溶剂， -15.0~20.0 ℃ 、344.74 kPa 条件下， 反应 14.5h， 生成 tert-butyl L-2-(tert-butoxycarbonyl)amino-4-(thioureidooxy)-butyrate
  参考文献：
  名称：

  Preparation and evaluation of new l-canavanine derivatives as nitric oxide synthase inhibitors

  摘要：

  New derivatives of the amino acid L-canavanine were prepared by total chemical synthesis and evaluated as inhibitors of inducible nitric oxide synthase (NOS). Replacement of the delta -methylene group of known NOS inhibitors with an oxygen atom produced dramatic effects as to the ability of these compounds to interact with the enzyme. These results indicate that the addition of an electron withdrawing group in the side chain of L-arginine-derived NOS inhibitors must be considered during inhibitor design depending on the expected mode of interaction with the enzyme. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00547-6

文献信息

• Preparation and evaluation of new l-canavanine derivatives as nitric oxide synthase inhibitors
  作者：Xiaofeng Li、Robert N Atkinson、S Bruce King

  DOI：10.1016/s0040-4020(01)00547-6

  日期：2001.7

  New derivatives of the amino acid L-canavanine were prepared by total chemical synthesis and evaluated as inhibitors of inducible nitric oxide synthase (NOS). Replacement of the delta -methylene group of known NOS inhibitors with an oxygen atom produced dramatic effects as to the ability of these compounds to interact with the enzyme. These results indicate that the addition of an electron withdrawing group in the side chain of L-arginine-derived NOS inhibitors must be considered during inhibitor design depending on the expected mode of interaction with the enzyme. (C) 2001 Elsevier Science Ltd. All rights reserved.