(3-Methoxy-phenylamino)-acetic acid tert-butyl ester | 139089-03-5

• 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: (3-Methoxy-phenylamino)-acetic acid tert-butyl ester
• 英文别名: tert-Butyl (3-methoxyphenyl)glycinate；tert-butyl 2-(3-methoxyanilino)acetate
• CAS: 139089-03-5
• 化学式: C₁₃H₁₉NO₃
• mdl: MFCD12650999
• 分子量: 237.299
• InChiKey: VGZXCIBQLPZKTF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.461
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3-Methoxy-phenylamino)-acetic acid tert-butyl ester 在 吡啶 、 硝酸 、 乙酸酐 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  N-Acyl-N-carboxymethyl-2-nitroaniline and its analogues: a new class of water-soluble photolabile precursor of carboxylic acids

  摘要：

  本文描述了新型水溶性光不稳定保护基团N-羧甲基-2-硝基苯胺基（CNA）的合成和光化学性质。合成的三种CNA笼型化合物在水缓冲溶液中均发生了清洁的光化学反应，产生了预期的乙酸产物以及相应的亚硝基芳香族化合物。

  DOI：

  10.1039/c2pp05322e
• 作为产物：
  描述：

  溴乙酸叔丁酯 、 间氨基苯甲醚 在 三乙胺 作用下， 以 乙醇 为溶剂， 生成 (3-Methoxy-phenylamino)-acetic acid tert-butyl ester
  参考文献：
  名称：

  Angiotensin-converting enzyme inhibitors. New orally active antihypertensive (mercaptoalkanoyl)- and [(acylthio)alkanoyl]glycine derivatives

  摘要：

  A variety of N-substituted (mercaptoalkanoyl)- and [(acylthio)alkanoyl]glycine derivatives was synthesized and their ability in inhibiting the activity of angiotensin-converting enzyme (ACE) was examined in vitro and in vivo. The acylthio derivatives prepared are assumed to act as prodrugs since they are much less active than the corresponding free SH compounds in vitro and can be expected to act in vivo only after conversion to the free sulfhydryl compounds. A number of these compounds are potent ACE inhibitors that lowered blood pressure in Na-deficient, conscious spontaneously hypertensive rats (SHR), a high renin model. One of the most active members of the series was (S)-N-cyclopentyl-N-[3-[(2,2-dimethyl-1-oxopropyl)thio]-2-methyl-1 -oxopropyl]glycine (REV 3659-(S), pivopril). Structure-activity relationships are discussed.

  DOI：

  10.1021/jm00379a013

文献信息

• US5475106A
  申请人：——

  公开号：US5475106A

  公开（公告）日：1995-12-12
• [EN] CONFORMATIONALLY CONSTRAINED MACROCYCLIC COMPOUNDS<br/>[FR] COMPOSÉS MACROCYCLIQUES À CONFORMATION LIMITÉE
  申请人：POLYPHOR AG

  公开号：WO2017063755A1

  公开（公告）日：2017-04-20

  Formula (I); Conformationally constrained macrocyclic compounds of formula (I), including substituents E with at least one ester moiety, G and Q, as defined in the description and the claims, and salts thereof, can be metabolized to compounds that have the property to modulate the activity of the peptidyl-prolyl cis/trans isomerase Pin1. In addition, they show antiproliferative activity on various cancer cell lines. Thus, these compounds and pharmaceutical compositions containing said compounds may be useful in the treatment and/or prevention of diseases or conditions in the area of proliferative disorders and diseases, such as e.g. cancer, inflammatory diseases, transplant rejection, viral infections, osteolytic bone diseases, cardiac diseases, cardiovascular diseases, respiratory diseases, acute neurological diseases, neurodegenerative diseases, immune disorders, and lymphoproliferative theileriosis.
• [EN] CONFORMATIONALLY CONSTRAINED MACROCYCLIC COMPOUNDS AS PIN1 MODULATORS<br/>[FR] UTILISATION DE COMPOSÉS MACROCYCLIQUES À CONFORMATION LIMITÉE COMME MODULATEURS DE PIN1
  申请人：POLYPHOR AG

  公开号：WO2017063754A1

  公开（公告）日：2017-04-20

  Conformationally constrained macrocyclic compounds of formula (I), including substituents E, G, and Q, as defined in the description and the claims, and salts thereof, have the property to modulate the activity of the peptidyl-prolyl cis/trans isomerases Pin1. Thus, these compounds and pharmaceutical compositions containing said compounds may be useful in the treatment and/or prevention of diseases or conditions in the area of proliferative disorders and diseases, such as e.g. cancer, inflammatory diseases, transplant rejection, viral infections, osteolytic bone diseases, cardiac diseases, cardiovascular diseases, respiratory diseases, acute neurological diseases, neurodegenerative diseases, immune disorders, and lymphoproliferative theileriosis.
• Angiotensin-converting enzyme inhibitors. New orally active antihypertensive (mercaptoalkanoyl)- and [(acylthio)alkanoyl]glycine derivatives
  作者：John T. Suh、Jerry W. Skiles、Bruce E. Williams、Raymond D. Youssefyeh、Howard Jones、Bernard Loev、Edward S. Neiss、Alfred Schwab、William S. Mann

  DOI：10.1021/jm00379a013

  日期：1985.1

  A variety of N-substituted (mercaptoalkanoyl)- and [(acylthio)alkanoyl]glycine derivatives was synthesized and their ability in inhibiting the activity of angiotensin-converting enzyme (ACE) was examined in vitro and in vivo. The acylthio derivatives prepared are assumed to act as prodrugs since they are much less active than the corresponding free SH compounds in vitro and can be expected to act in vivo only after conversion to the free sulfhydryl compounds. A number of these compounds are potent ACE inhibitors that lowered blood pressure in Na-deficient, conscious spontaneously hypertensive rats (SHR), a high renin model. One of the most active members of the series was (S)-N-cyclopentyl-N-[3-[(2,2-dimethyl-1-oxopropyl)thio]-2-methyl-1 -oxopropyl]glycine (REV 3659-(S), pivopril). Structure-activity relationships are discussed.
• N-Acyl-N-carboxymethyl-2-nitroaniline and its analogues: a new class of water-soluble photolabile precursor of carboxylic acids
  作者：Takuya Honda、Atsuya Momotake、Tatsuo Arai

  DOI：10.1039/c2pp05322e

  日期：2012.3

  The synthesis and photochemistry of a new class of water-soluble, photolabile protecting group, the N-carboxymethyl-2-nitroanilinyl (CNA) group, are described. All three CNA-caging compounds synthesized underwent clean photochemical reaction in aqueous buffer solution to produce the intended product of acetic acid, along with the corresponding nitroso aromatic.

  本文描述了新型水溶性光不稳定保护基团N-羧甲基-2-硝基苯胺基（CNA）的合成和光化学性质。合成的三种CNA笼型化合物在水缓冲溶液中均发生了清洁的光化学反应，产生了预期的乙酸产物以及相应的亚硝基芳香族化合物。