Ethyl (S)-2-(tert-butoxycarbonylamino)-5-oxo-5-(p-tolyl)pentanoate | 153783-21-2

• 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: Ethyl (S)-2-(tert-butoxycarbonylamino)-5-oxo-5-(p-tolyl)pentanoate
• 英文别名: ethyl (2S)-5-(4-methylphenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-5-oxopentanoate
• CAS: 153783-21-2
• 化学式: C₁₉H₂₇NO₅
• 分子量: 349.427
• InChiKey: NDLQSYSLZFJBIK-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  25
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  81.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Ethyl (S)-2-(tert-butoxycarbonylamino)-5-oxo-5-(p-tolyl)pentanoate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以87%的产率得到(S)-5-Ethoxycarbonyl-2-(p-tolyl)-Δ¹-pyrroline
  参考文献：
  名称：

  合成5-芳基吡咯-2-羧酸的通用方法

  摘要：

  5-芳基吡咯-2-羧酸是由相应的2-芳基- Δ的DDQ氧化芳构化制备1吡咯啉-5-羧酸乙酯，随后碱性水解。

  DOI：

  10.1016/s0040-4039(00)73741-5
• 作为产物：
  描述：

  BOC-L-焦谷氨酸乙酯 、 对甲苯基溴化镁 以 四氢呋喃 为溶剂， 以78%的产率得到Ethyl (S)-2-(tert-butoxycarbonylamino)-5-oxo-5-(p-tolyl)pentanoate
  参考文献：
  名称：

  合成5-芳基吡咯-2-羧酸的通用方法

  摘要：

  5-芳基吡咯-2-羧酸是由相应的2-芳基- Δ的DDQ氧化芳构化制备1吡咯啉-5-羧酸乙酯，随后碱性水解。

  DOI：

  10.1016/s0040-4039(00)73741-5

文献信息

• General method for the synthesis of 5-arylpyrrole-2-carboxylic acids
  作者：Jesús Ezquerra、Concepción Pedregal、Almudena Rubio、Jesús Valenciano、José Luis García Navio、Julio Alvarez-Builla、Juan José Vaquero

  DOI：10.1016/s0040-4039(00)73741-5

  日期：1993.9

  5-Arylpyrrole-2-carboxylic acids are prepared by DDQ oxidative aromatization of the corresponding ethyl 2-aryl-Δ1-pyrroline-5-carboxylate followed by basic hydrolysis.

  5-芳基吡咯-2-羧酸是由相应的2-芳基- Δ的DDQ氧化芳构化制备1吡咯啉-5-羧酸乙酯，随后碱性水解。
• Convenient synthesis of C-aza-2,3-dideoxynucleosides
  作者：Atsuya Momotake、Hideo Togo、Masataka Yokoyama

  DOI：10.1039/a900689c

  日期：——

  1-Aryl-1,2,3,4-tetradeoxy-1,4-imino-D-pentitols 5 and 9f are easily synthesized from N-Boc-L-pyroglutamate 1 via a successive procedure involving regioselective ring-opening, recyclization with dehydration, stereoselective reduction, and reduction of the ester group. Their structures are determined mainly by X-ray crystallography and NMR measurements. Their bioassay is also described.

  1- 芳基-1,2,3,4-四甲氧基-1,4-亚氨基-D-戊醇 5 和 9f 是由 N-Boc-L-pyroglutamate 1 通过区域选择性开环、脱水再化、立体选择性还原和酯基还原等连续过程轻松合成的。它们的结构主要是通过 X 射线晶体学和核磁共振测量确定的。此外，还介绍了它们的生物测定方法。
• Design of Orally Active Dual Inhibitors of Neutral Endopeptidase and Angiotensin-Converting Enzyme with Long Duration of Action
  作者：Marie-Claude Fournie-Zaluski、Pascale Coric、Vincent Thery、Walter Gonzalez、Hervé Meudal、Serge Turcaud、Jean-Baptiste Michel、Bernard P. Roques

  DOI：10.1021/jm950783c

  日期：1996.1.1

  Mercaptoacyl dipeptides, containing a glycine Linked to a C-terminal 5-phenylproline, have been synthesized in order to obtain new highly efficient dual inhibitors of the two zinc metallopeptidases, neutral endopeptidase (NEP) and angiotensin-converting enzyme (ACE), which are involved in the control of blood pressure and fluid homeostasis. These compounds have been designed (i) to fit optimally the ACE pharmacophore previously described (Fournie-Zaluski, M. C.; et al. J. Med. Chem. 1994, 37, 1070-1083), through interaction with the S-1, S-1', and S-2' subsites of this enzyme, (ii) and to interact with the S-1' and S-2' subsites of NEP with the 5-phenylproline moiety outside the catalytic domain (Coric, P.; et al. J. Med. Chem. 1996, 39, 1210-1219). Replacement of Gly by Ala in these mercaptoacyl dipeptides induced an about 100-fold decreasein ACE inhibition. This shows that, in agreement with molecular modeling studies, a steric constraint as weak as a methyl group hinders optimal ACE active site recognition, Among these compounds, the dual inhibitor 26 (RB 106) (K-i, ACE =: 0.35 nM; NEP = 1.6 nM) showed excellent pharmacokinetic properties with an almost complete in vivo inhibition of NEP and ACE for more than 4 h after oral administration in mice of a low dose (2.6 x 10(-5) mol/kg) of the inhibitor. Moreover, RE 106 remained active 12 h after oral administration In spontaneous hypertensive rats, a chronic treatment of orally administered RB 106 (25 mg/kg/day) induced a prolonged hypotensive effect (-28 mmHg) still significant 2 days after the end of the treatment. In DOCA salt rats, a hypotensive response and a significant natriuresis were observed after iv administration RE 106, which is one of the most potent dual inhibitors described to date, could have interesting clinical applications in long term treatment of congestive heart failure and myocardial ischemia.