methyl (2S)-2-[(4-methylphenyl)sulfonylamino]-3-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate | 169604-92-6

• 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: methyl (2S)-2-[(4-methylphenyl)sulfonylamino]-3-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate
• CAS: 169604-92-6
• 化学式: C₁₆H₂₄N₂O₆S
• 分子量: 372.442
• InChiKey: ALVFCIGWBNQCGC-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  119
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl (2S)-2-[(4-methylphenyl)sulfonylamino]-3-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate 在 盐酸 、 potassium carbonate 、 三乙胺 作用下， 以 1,4-二氧六环 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 (S)-3-[3-(4-Cyano-phenoxymethyl)-benzoylamino]-2-(toluene-4-sulfonylamino)-propionic acid methyl ester
  参考文献：
  名称：

  Design, synthesis, and in vitro activities of benzamide-core glycoprotein IIb/IIIa antagonists: 2,3-Diaminopropionic acid derivatives as surrogates of aspartic acid

  摘要：

  In an effort to discover novel nonpeptide glycoprotein IIb/IIIa (GPIIb/lIIa, alpha(IIb)/beta 3) inhibitors, we investigated RGD mimetics featuring a 3-substituted benzoic acid as the core, benzamidine as the basic moiety, and a series of beta- and alpha-substituted beta-alanine derivatives as aspartic acid surrogates. It was found that the use of beta-methyl beta-alanine slightly improved the anti-aggregant potency in human platelet-rich plasma over the unsubstituted beta-alanine compound, while alpha-substitution with a trifluoromethyl group resulted in considerable loss in activity. Significant enhancement (up to 100-fold) in potency was obtained when the beta-alanine was replaced with N-2-substituted L-2,3-diaminopropionic acid derivatives. Among the three types of cc-substituents (carbamate, amide, and sulfonamide) investigated, no apparent preference was observed with respect to in vitro potency. However, alkyl groups were more favorable than arylalkyl groups (Cbz) in the carbamate analogues. We also investigated piperidine, piperazine, and N-formamidinopiperidine as replacements for the benzamidine moiety. The former two replacements led to a drop in potency while the latter replacement resulted in maintenance of activity as compared with the corresponding benzamidine analogue. (C) 1997 The DuPont Merck Pharmaceutical Company. Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(97)00013-8
• 作为产物：
  描述：

  (S)-2-N-Cbz-3-N-Boc-丙酸甲酯 在 palladium on activated charcoal 氢气 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 氯仿 为溶剂， 生成 methyl (2S)-2-[(4-methylphenyl)sulfonylamino]-3-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate
  参考文献：
  名称：

  Design, synthesis and in vitro activities of a series of benzimidazole/benzoxazole glycoprotein IIb/IIIa inhibitors

  摘要：

  A potent centrally constrained series of benzimidazole and benzoxazole glycoprotein IIb/IIIa inhibitors has been discovered based on the solution conformation of a cyclic RGD-containing peptide, DMP 728. The high potency of this series of compounds in the inhibition of platelet aggregation requires a benzamidine as the basic moiety and an alpha-carbamate or sulfonamide substituted beta-alanine as the acidic moiety.

  DOI：

  10.1016/0960-894x(95)00590-p

文献信息

• Asymmetric synthesis of (<i>R</i>)-6-amino-1-methyl-4-(3-methyl-benzyl)hexahydro-1<i>H</i>-1,4-diazepine from L-asparagine
  作者：Shiro Kato、Hiroshi Harada、Toshiya Mode

  DOI：10.1002/jhet.5570340516

  日期：1997.9

  hexahydro-1H-1,4-diazepine ring was achieved by the intramolecular ami-dation of the optically active aminocarboxylic acid 18 or reductive cyclization of the optically active aminoaldehyde 25. Compounds 18 and 25 were prepared from L-asparagine via the key aziridine derivatives 15 and 22, respectively, with retention of the configuration. The intramolecular aziridine ring opening reaction of 29 gave the

  有效的不对称合成（R）-6-氨基-1-甲基-4-（3-甲基乙基苄基）六氢-1 H -1,4-二氮杂[[ R -2）]用作（R的胺部分）-1，一种有效且选择性的5-HT 3受体拮抗剂。的六氢形成ħ环二氮杂-1,4是由光学活性的氨基羧酸的分子内AMI-dation实现18或还原性环化的光学活性氨基醛25化合物18和25从L-天冬酰胺，制备经由关键氮丙啶衍生物15和22，分别保留配置。分子内氮丙啶开环反应29得到的是氮丙啶环的C 2 N键裂解产物哌嗪5一30作为主要产物，以及所需的7元环hexahydro-1 H -1， 4-二氮杂product产品19。