ethyl 2-indan-2-ylpropenoate | 143700-90-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: ethyl 2-indan-2-ylpropenoate
• 英文别名: ethyl 2-(2,3-dihydro-1H-inden-1-yl)prop-2-enoate
• CAS: 143700-90-7
• 化学式: C₁₄H₁₆O₂
• 分子量: 216.28
• InChiKey: OYMOBXBDARCWIU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ethyl 2-indan-2-ylpropenoate 在 sodium hydroxide 作用下， 以 氯仿 、 丙酮 为溶剂， 反应 24.0h， 生成 (2S)-3-acetylsulfanyl-2-[(1R)-2,3-dihydro-1H-inden-1-yl]propanoic acid
  参考文献：
  名称：

  Toward an Optimal Joint Recognition of the S₁‘ Subsites of Endothelin Converting Enzyme-1 (ECE-1), Angiotensin Converting Enzyme (ACE), and Neutral Endopeptidase (NEP)

  摘要：

  The formation of vasoconstrictors (e.g., angiotensin II and endothelin) and the inactivation of vasodilators (e.g., bradykinin and atrial natriuretic) by membrane-bound zinc metallopeptidases are key mechanisms in the control of blood pressure and fluid homeostasis. The way in which these peptides modulate physiological functions has been intensively studied. With the aim to develop compounds that can jointly block the three metallopeptidases-neutral endopeptidase (NEP, neprilysin), angiotensin-converting enzyme (ACE), and endothelin-converting enzyme (ECE-1)-we studied the common structural specificity of the S-1' subsites of these peptidases. Various mercaptoacyl amino acids of the general formula HS-CH2-CH(R-1')CO-Trp-OH, possessing more or less constrained R-1' side chains, were designed. The mercapto-acyl synthons contain one or two asymmetrical centers. The K-i values of the separated stereoisomers of the most efficient inhibitors were used to determine the stereochemical preference of each enzyme. A guideline for the joint inhibition of the three peptidases was obtained with the (2R,3R) isomer of compound 13b. Its K-i values on NEP, ACE, and ECE were 0.7, 43, and 26 nM, respectively.

  DOI：

  10.1021/jm0005454
• 作为产物：
  描述：

  聚合甲醛 、 2-(diethoxyphosphoryl)-(indan-1-yl)-acetic acid ethyl ester 在 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 ethyl 2-indan-2-ylpropenoate
  参考文献：
  名称：

  Toward an Optimal Joint Recognition of the S₁‘ Subsites of Endothelin Converting Enzyme-1 (ECE-1), Angiotensin Converting Enzyme (ACE), and Neutral Endopeptidase (NEP)

  摘要：

  The formation of vasoconstrictors (e.g., angiotensin II and endothelin) and the inactivation of vasodilators (e.g., bradykinin and atrial natriuretic) by membrane-bound zinc metallopeptidases are key mechanisms in the control of blood pressure and fluid homeostasis. The way in which these peptides modulate physiological functions has been intensively studied. With the aim to develop compounds that can jointly block the three metallopeptidases-neutral endopeptidase (NEP, neprilysin), angiotensin-converting enzyme (ACE), and endothelin-converting enzyme (ECE-1)-we studied the common structural specificity of the S-1' subsites of these peptidases. Various mercaptoacyl amino acids of the general formula HS-CH2-CH(R-1')CO-Trp-OH, possessing more or less constrained R-1' side chains, were designed. The mercapto-acyl synthons contain one or two asymmetrical centers. The K-i values of the separated stereoisomers of the most efficient inhibitors were used to determine the stereochemical preference of each enzyme. A guideline for the joint inhibition of the three peptidases was obtained with the (2R,3R) isomer of compound 13b. Its K-i values on NEP, ACE, and ECE were 0.7, 43, and 26 nM, respectively.

  DOI：

  10.1021/jm0005454

文献信息

• N-(mercaptoacyl)amino acids, methods of their preparation and therapeutic use, and pharmaceutical compositions containing them
  申请人：INSTITUT NATIONAL DE LA SANTE ET DE LA RECHERCHE MEDICALE (INSERM)

  公开号：EP0539848A1

  公开（公告）日：1993-05-05

  The present invention is directed to a compound of the formula (I) wherein    R represents a hydrogen atom or an acyl, aroyl or cycloalkylcarbonyl radical or a residue of formula    R₁ represents an alkyl radical;    R₂ represents an aryl or heteroaryl radical, or R₁ represents an alkylene chain attached to a carbon atom in an ortho position of the R₂ aryl or heteroaryl radical relative to a carbon of the R₂ aryl or heteroaryl radical linked to the propanoyl moiety;    R₃ represents a hydrogen atom or an alkyl, aryl, alkoxy or aryloxy radical; and    R' represents a hydrogen atom or an alkyl, aralkyl, acyl or aroyl radical;    and the pharmaceutically acceptable salts thereof. The invention is also directed to the preparation of these compounds, pharmaceutical compositions comprising the compounds and methods for their pharmaceutical use.

  本发明涉及一种式（I）的化合物，其中： R代表氢原子或酰基、芳酰基或环烷基羰基基团，或者是式中的残基 R₁代表烷基基团； R₂代表芳基或杂芳基基团，或者R₁代表连接到R₂芳基或杂芳基相对于连接到丙酰基基团的R₂芳基或杂芳基的碳原子的烷基链； R₃代表氢原子或烷基、芳基、烷氧基或芳氧基基团； R'代表氢原子或烷基、芳基烷基、酰基或芳酰基基团； 以及其药学上可接受的盐。本发明还涉及这些化合物的制备、包含这些化合物的制药组合物以及它们的制药用途的方法。
• Palladium-Catalyzed Intramolecular Cyclization of Vinyl and Aryl Triflates. Associated Regioselectivity of the beta-Hydride Elimination Step.
  作者：Shaowo Liang、Leo A. Paquette、C. Oliver Kappe、Regis Leung-Toung、Curt Wentrup、Jørgen B. Pedersen、Povl Krogsgaard-Larsen

  DOI：10.3891/acta.chem.scand.46-0597

  日期：——

  Pd(0)-catalyzed intramolecular olefination of vinyl and aryl triflates has been studied with a view to gaining insight into the question of kinetically preferred reductive elimination when at least two options are available. In either series, a non-activated alkene participant was found to be converted most readily into the non-conjugated cyclization product. This trend is seen despite the more forcing conditions

  已经研究了Pd（0）催化的乙烯基和芳基三氟甲磺酸酯的分子内烯化反应，以便在至少有两种选择的情况下获得对动力学上优选的还原消除的认识。在任一系列中，发现未活化的烯烃参加者最容易转化成非共轭环化产物。尽管在闭环过程中要使用反应性较低的芳基三氟甲磺酸酯所需的条件更强，但仍可看到这种趋势。另一方面，当侧链由α-丙烯酸甲酯单元终止时，在动力学上优选共轭二烯。这两个反应似乎在能量上紧密平衡，因为产品分布并没有很大的不同。不过，
• [EN] N-(MERCAPTOACYL)AMINO ACIDS, METHODS OF THEIR PREPARATION AND THERAPEUTIC USE, AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM
  申请人：INSTITUT NATIONAL DE LA SANTE ET DE LA RECHERCHE MEDICALE (INSERM)

  公开号：WO1993008162A1

  公开（公告）日：1993-04-29

  (EN) The present invention is directed to a compound of formula (I), wherein R represents a hydrogen atom or an acyl, aroyl or cycloalkylcarbonyl radical or a residue of formula (Ia); R1 represents an alkyl radical; R2 represents an aryl or heteroaryl radical, or R1 represents an alkylene chain attached to a carbon atom in an ortho position of the R2 aryl or heteroaryl radical relative to a carbon of the R2 aryl or heteroaryl radical linked to the propanoyl moiety; R3 represents a hydrogen atom or an alkyl, aryl, alkoxy or aryloxy radical; and R' represents a hydrogen atom or an alkyl, aralkyl, acyl or aroyl radical; and the pharmaceutically acceptable salts thereof. The invention is also directed to the preparation of these compounds, pharmaceutical compositions comprising the compounds and methods for their pharmaceutical use.(FR) Composé répondant à la formule (I), dans laquelle R représente un atome d'hydrogène ou un radical acyle, aroyle ou cycloalkylcarbonyle, ou un reste répondant à la formule (Ia); R1 représente un radical alkyle; R2 représente un radical aryle ou hétéroaryle, ou R1 représente une chaîne alkylène fixée à un atome de carbone dans une position ortho du radical aryle ou hétéroaryle R2 lié à la fraction propanoyle; R3 représente un atome d'hydrogène ou un radical alkyle, aryle, alcoxy ou aryloxy; et R' représente un atome d'hydrogène ou un radical alkyle, aralkyle, acyle ou aroyle; et ses sels pharmaceutiquement acceptables. On a également prévu la préparation de ces composés, les compositions pharmaceutiques contenant ces composés, et leurs procédés d'utilisation pharmaceutique.

  该发明涉及一种化合物，其化学式为(I)，其中R代表氢原子或酰基、芳基或环烷基羧酰基基团或式(Ia)的残基；R1代表烷基基团；R2代表芳基或杂环芳基基团，或者R1代表连接到R2芳基或杂环芳基基团的一个碳原子的烷基链，该碳原子与连接到丙酰基基团的R2芳基或杂环芳基基团的碳原子相对；R3代表氢原子或烷基、芳基、烷氧基或芳氧基基团；R'代表氢原子或烷基、芳基烷基、酰基或芳基酰基基团；以及其药学上可接受的盐。该发明还涉及这些化合物的制备、包含这些化合物的药物组合物以及它们的药物用途的方法。
• N-(MERCAPTOACYL)AMINO ACIDS, METHODS OF THEIR PREPARATION AND THERAPEUTIC USE, AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM
  申请人：INSTITUT NATIONAL DE LA SANTE ET DE LA RECHERCHE MEDICALE (INSERM)

  公开号：EP0609310A1

  公开（公告）日：1994-08-10
• US5591891A
  申请人：——

  公开号：US5591891A

  公开（公告）日：1997-01-07