indol-3-yl-pyruvic acid ethyl ester | 32817-17-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: indol-3-yl-pyruvic acid ethyl ester
• 英文别名: Indol-3-yl-brenztraubensaeure-aethylester；3-(1H-indol-3-yl)-2-oxo-propionic acid ethyl ester；3-indolepyruvic acid ethyl ester；(Indolyl-3)-brenztraubensaeure-ethylester；ethyl 3-(1H-indol-3-yl)-2-oxopropanoate
• CAS: 32817-17-7
• 化学式: C₁₃H₁₃NO₃
• 分子量: 231.251
• InChiKey: OYZDYSMWNUUSAK-UHFFFAOYSA-N

物化性质

• 熔点：
  149-150 °C
• 沸点：
  419.9±28.0 °C(Predicted)
• 密度：
  1.251±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  59.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  indol-3-yl-pyruvic acid ethyl ester 生成 3-(3-吲哚基)-2-氧代丙酸
  参考文献：
  名称：

  Ratusky; Sorm, Collection of Czechoslovak Chemical Communications, 1958, vol. 23, p. 467,472

  摘要：

  DOI：
• 作为产物：
  描述：

  溴乙烷 、 3-(3-吲哚基)-2-氧代丙酸 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 苯 为溶剂， 以70%的产率得到indol-3-yl-pyruvic acid ethyl ester
  参考文献：
  名称：

  3-indolepyruvic acid derivatives and pharmaceutical use thereof

  摘要：

  本发明涉及3-吲哚丙酸衍生物，以及治疗中枢神经系统扰动的组合物和方法，因为存在过多的兴奋性氨基酸。

  公开号：

  US05002963A1

文献信息

• Carboxyalkyl dipeptides
  申请人：Schering Corporation

  公开号：US05348944A1

  公开（公告）日：1994-09-20

  Compounds of the formula ##STR1## useful as antihypertensive agents are disclosed.

  公开了化学式为##STR1##的化合物，其作为降压剂具有用途。
• Novel Inhibitors of Glutaminyl Cyclase
  申请人：Thormann Michael

  公开号：US20090269301A1

  公开（公告）日：2009-10-29

  The present invention relates to compounds of formula (I), combinations and uses thereof for disease therapy, R 1 represents heteroaryl, -carbocyclyl-heteroaryl, -alkenylheteroaryl or -alkylheteroaryl; R 2 represents hydrogen; halogen; alkenyl; alkynyl; -alkenylaryl; -alkenylheteroaryl; alkyl, which may optionally be substituted by one or more groups selected from halogen, hydroxyl, alkoxy-, -thioalkyl, —C(O)OH and —C(O)O-alkyl; carbocyclyl, which may optionally be substituted by one or more groups selected from alkyl, halogen, hydroxyl, alkoxy-, -thioalkyl, —C(O)OH and —C(O)O-alkyl; -alkylcarbocyclyl; -alkylheterocyclyl; aryl; heteroaryl; heterocyclyl; -alkylaryl; -alkyl(aryl) 2 , -alkylheteroaryl; -aryl-heteroaryl; -heterocyclyl-aryl; -aryl-aryl; -heteroaryl-aryl; -heteroaryl-heteroaryl, and —C(O)R 4 ; R 3 represents halogen; alkyl optionally substituted by one or more groups selected from halogen, hydroxyl, alkoxy, thioalkyl, —C(O)OH and —C(O)O-alkyl; aryl; heteroaryl; —C(O)R 5 ; R 4 and R 5 independently represent alkyl, aryl, heteroaryl, -alkylaryl, -alkylheteroaryl, carbocyclyl, heterocyclyl, -alkylcarbocyclyl and -alkylheterocyclyl, with the proviso that, when R 1 is imidazolyl, -carbocyclyl-imidazolyl, -alkenyl-imidazolyl or -alkyl-imidazolyl, then R 3 may not be —C(O)R 5 .

  本发明涉及式（I）化合物，其组合物和用于疾病治疗的用途。其中，R1代表杂环芳基，-碳环芳基-杂环芳基，-烯基杂环芳基或-烷基杂环芳基；R2代表氢，卤素，烯基，炔基，-烯基芳基，-烯基杂环芳基，烷基，可以选择被一个或多个从卤素，羟基，烷氧基，硫代烷基，-C（O）OH和-C（O）O-烷基中选择的基团取代的烷基，可以选择被一个或多个从烷基，卤素，羟基，烷氧基，硫代烷基，-C（O）OH和-C（O）O-烷基中选择的基团取代的碳环芳基，可以选择被一个或多个从烷基，卤素，羟基，烷氧基，硫代烷基，-C（O）OH和-C（O）O-烷基中选择的基团取代的-烷基碳环芳基，-烷基杂环芳基，芳基，杂环芳基，杂环芳基，-烷基芳基2，-烷基杂环芳基，-芳基杂环芳基，-杂环芳基-芳基，-芳基-芳基，-杂环芳基-芳基，-杂环芳基-杂环芳基和-C（O）R4；R3代表卤素，烷基，可以选择被一个或多个从卤素，羟基，烷氧基，硫代烷基，-C（O）OH和-C（O）O-烷基中选择的基团取代的烷基，芳基，杂环芳基和-C（O）R5；R4和R5独立地代表烷基，芳基，杂环芳基，-烷基芳基，-烷基杂环芳基，碳环芳基，杂环芳基，-烷基碳环芳基和-烷基杂环芳基，但当R1是咪唑基，-碳环芳基-咪唑基，-烯基咪唑基或-烷基咪唑基时，R3不能是-C（O）R5。
• Inhibitors of glutaminyl cyclase
  申请人：Probiodrug AG

  公开号：US08278345B2

  公开（公告）日：2012-10-02

  The present invention relates to compounds of formula (I), combinations and uses thereof for disease therapy, R1 represents heteroaryl, -carbocyclyl-heteroaryl, -alkenylheteroaryl or -alkylheteroaryl; R2 represents hydrogen; halogen; alkenyl; alkynyl; -alkenylaryl; -alkenylheteroaryl; alkyl, which may optionally be substituted by one or more groups selected from halogen, hydroxyl, alkoxy-, -thioalkyl, —C(O)OH and —C(O)O-alkyl; carbocyclyl, which may optionally be substituted by one or more groups selected from alkyl, halogen, hydroxyl, alkoxy-, -thioalkyl, —C(O)OH and —C(O)O-alkyl; -alkylcarbocyclyl; -alkylheterocyclyl; aryl; heteroaryl; heterocyclyl; -alkylaryl; -alkyl(aryl)2, -alkylheteroaryl; -aryl-heteroaryl; -heterocyclyl-aryl; -aryl-aryl; -heteroaryl-aryl; -heteroaryl-heteroaryl, and —C(O)R4; R3 represents halogen; alkyl optionally substituted by one or more groups selected from halogen, hydroxyl, alkoxy, thioalkyl, —C(O)OH and —C(O)O-alkyl; aryl; heteroaryl; —C(O)R5; R4 and R5 independently represent alkyl, aryl, heteroaryl, -alkylaryl, -alkylheteroaryl, carbocyclyl, heterocyclyl, -alkylcarbocyclyl and -alkylheterocyclyl, with the proviso that, when R1 is imidazolyl, -carbocyclyl-imidazolyl, -alkenyl-imidazolyl or -alkyl-imidazolyl, then R3 may not be —C(O)R5.

  本发明涉及公式（I）化合物，其组合物和用于疾病治疗的用途，其中R1代表杂环芳基，-碳环芳基-杂环芳基，-烯基杂环芳基或-烷基杂环芳基；R2代表氢，卤素，烯基，炔基，-烯基芳基，-烯基杂环芳基，烷基，该烷基可以选择性地被一个或多个从卤素，羟基，烷氧基，硫代烷基，-C（O）OH和-C（O）O-烷基中选择的基团取代；碳环芳基，该碳环芳基可以选择性地被一个或多个从烷基，卤素，羟基，烷氧基，硫代烷基，-C（O）OH和-C（O）O-烷基中选择的基团取代；-烷基碳环芳基；-烷基杂环芳基；芳基；杂环芳基；杂环芳基；-烷基芳基2，-烷基杂环芳基；-芳基-杂环芳基；-杂环芳基-芳基；-芳基-芳基；-杂环芳基-芳基；-杂环芳基-杂环芳基，和-C（O）R4；R3代表卤素；烷基，该烷基可以选择性地被一个或多个从卤素，羟基，烷氧基，硫代烷基，-C（O）OH和-C（O）O-烷基中选择的基团取代；芳基；杂环芳基；-C（O）R5；R4和R5独立地表示烷基，芳基，杂环芳基，-烷基芳基，-烷基杂环芳基，碳环芳基，杂环芳基，-烷基碳环芳基和-烷基杂环芳基，但是当R1为咪唑基，-碳环芳基-咪唑基，-烯基咪唑基或-烷基咪唑基时，R3不能为-C（O）R5。
• Carboxyalkyl dipeptides, processes for their production and pharmaceutical compositions containing them
  申请人：SCHERING CORPORATION

  公开号：EP0050800A1

  公开（公告）日：1982-05-05

  Disclosed are novel carboxyalkyl dipeptides which are useful as inhibitors of angiotensinconverting enzyme and as antihypertensive agents, having the formula and the pharmaceutically acceptable salts thereof, wherein R and R6 are for example hydroxy, lower alkoxy or arylloweralkoxy; R' is for example hydrogen, alkyl, lower alkoxy or aryloxy; R2 and R are the same or different and are hydrogen or lower alkyl; R3 is for example lower alkyl or phenyl lower alkyl; R4 and R5 are selected from hydrogen, lower alkyl and Z, or R4 and R5 taken together form a group represented by Q, U, V, Y, D or E wherein wherein X' and X2 independent of each other are 0, S or CH2, R8 and R9 independent of each other are lower alkyl, lower alkenyl, lower alkynyl, cycloalkyl having 3 to 8 carbon atoms, hydroxy lower alkyl or -(CH2)nAr, wherein n is 0, 1, 2 or 3 or R8 and R9 taken together form a bridge W, wherein W is a single bond or a methylene bridge or a substituted methylene bridge when at least one of X' and X2 is methylene, or W is an alkylene or substituted alkylene bridge having 2 or 3 carbon atoms; with the proviso that at least one of R4 and R5 is Z; wherein L is O or S. The compounds can be prepared according to known methods such as for example by condensation of an aminoacid XXI with an aminoacid XVII wherein X1, X2 and W are as defined above; wherein G is oxygen, sulfur or CH2;

  本发明公开了可用作血管紧张素转换酶抑制剂和降压药的新型羧烷基二肽，其化学式为 其中 R 和 R6 例如是羟基、低级烷氧基或芳基低级烷氧基；R'例如是氢、烷基、低级烷氧基或芳基氧基；R2 和 R 相同或不同，并且是氢或低级烷基；R3 例如是低级烷基或苯基低级烷基；R4 和 R5 选自氢、低级烷基和 Z，或 R4 和 R5 共同形成由 Q、U、V、Y、D 或 E 代表的基团，其中 其中 X' 和 X2 互不相关，分别为 0、S 或 CH2，R8 和 R9 互不相关，分别为低级烷基、低级烯基、低级炔基、具有 3 至 8 个碳原子的环烷基、羟基低级烷基或-(CH2)nAr，其中 n 为 0、1、其中 W 是单键或亚甲基桥或取代的亚甲基桥（当 X' 和 X2 中至少有一个是亚甲基时），或 W 是具有 2 或 3 个碳原子的亚烷基或取代的亚烷基桥；但 R4 和 R5 中至少有一个是 Z； 这些化合物可根据已知方法制备，例如通过氨基酸 XXI 与氨基酸 XVII 缩合 其中 X1、X2 和 W 如上定义； 其中 G 为氧、硫或 CH2；
• METHOD FOR PURIFYING PYRUVIC ACID COMPOUNDS
  申请人：SUMITOMO CHEMICAL COMPANY LIMITED

  公开号：EP0937703A1

  公开（公告）日：1999-08-25

  The present invention is directed to a method for purifying pyruvic acid compounds, which method comprises reacting a pyruvic acid compound of general formula (I): wherein R1 is an optionally substituted lower alkyl group, a lower alkenyl group, a lower alkynyl group, a cycloalkyl group, an aryl group, or a heterocyclic group, and R2 is a lower alkyl group, with a bisulfite of general formula (II):         MHSO3     (II) wherein M is NH4 or an alkali metal, to give a bisulfite adduct of the pyruvic acid compound and then decomposing the adduct with an acid. According to the present invention, pyruvic acid compounds can be purified by simple and easy procedures without using purification techniques such as distillation or column chromatography, and the above method is advantageous as a process for the production on an industrial scale.

  本发明涉及一种纯化丙酮酸化合物的方法，该方法包括使通式(I)的丙酮酸化合物反应： 其中 R1 是任选取代的低级烷基、低级烯基、低级炔基、环烷基、芳基或杂环基，R2 是低级烷基，与通式（II）的亚硫酸氢盐反应： MHSO3 (II) 其中 M 为 NH4 或碱金属，以得到丙酮酸化合物的亚硫酸氢盐加合物，然后用酸分解该加合物。根据本发明，丙酮酸化合物可以通过简单易行的程序进行纯化，而无需使用蒸馏或柱层析等纯化技术，上述方法作为一种工业规模的生产工艺是非常有利的。