5-(对乙氧基羰基苯基)-咪唑并[1,5-a]吡啶 | 93178-58-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 5-(对乙氧基羰基苯基)-咪唑并[1,5-a]吡啶
• 英文名称: 5-(p-ethoxycarbonylphenyl)-imidazo[1,5-a]pyridine
• 英文别名: 5-<4-(ethoxycarbonyl)phenyl>imidazo<1,5-a>pyridine；ethyl 4-(imidazo[1,5-a]pyridin-5-yl)benzoate；5-(p-ethoxycarbonylphenyl)imidazo[1,5-a]pyridine；ethyl 4-imidazo[1,5-a]pyridin-5-ylbenzoate
• CAS: 93178-58-6
• 化学式: C₁₆H₁₄N₂O₂
• 分子量: 266.299
• InChiKey: CBBNWSFYMXZPOX-UHFFFAOYSA-N

物化性质

• 熔点：
  118-119 °C
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  43.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(对乙氧基羰基苯基)-咪唑并[1,5-a]吡啶 在 palladium on activated charcoal 盐酸 、 sodium hydroxide 、 氯化亚砜 、 氨 、 氢气 、 三氯氧磷 作用下， 以 乙醇 、 二氯甲烷 、 氯仿 为溶剂， 60.0 ℃ 、275.79 kPa 条件下， 反应 37.5h， 生成 法倔唑
  参考文献：
  名称：

  Fadrozole hydrochloride: a potent, selective, nonsteroidal inhibitor of aromatase for the treatment of estrogen-dependent disease

  摘要：

  A new class of potent, selective, nonsteroidal inhibitors of aromatase have been discovered. The most potent member of this series is fadrozole hydrochloride, CGS 16949 A, 4-(5,6,7,8-tetrahydroimidazo[1,5-a]pyridin-5-yl)benzonitrile monohydrochloride, 26a. In addition, the 6,7-dihydropyrrolo[1,2-c]imidazole (21a) and the 6,7,8,9-tetrahydroimidazo[1,5-a]azepine (21b) analogues were synthesized and evaluated. CGS 16949 A's ability to selectively inhibit aromatase (IC50 = 4.5nM) over other cytochrome P-450 enzymes and suppress estrogen production when administered orally make it a suitable candidate to test the potential of an aromatase inhibitor in estrogen-dependent diseases including breast cancer.

  DOI：

  10.1021/jm00106a038
• 作为产物：
  描述：

  2-<4-(ethoxycarbonyl)phenyl>pyridine N-oxide 在 palladium on activated charcoal 盐酸 、 氢气 、 硫酸二甲酯 、 三氯氧磷 作用下， 以 甲醇 、 甲苯 为溶剂， 90.0 ℃ 、101.33 kPa 条件下， 反应 57.0h， 生成 5-(对乙氧基羰基苯基)-咪唑并[1,5-a]吡啶
  参考文献：
  名称：

  Fadrozole hydrochloride: a potent, selective, nonsteroidal inhibitor of aromatase for the treatment of estrogen-dependent disease

  摘要：

  A new class of potent, selective, nonsteroidal inhibitors of aromatase have been discovered. The most potent member of this series is fadrozole hydrochloride, CGS 16949 A, 4-(5,6,7,8-tetrahydroimidazo[1,5-a]pyridin-5-yl)benzonitrile monohydrochloride, 26a. In addition, the 6,7-dihydropyrrolo[1,2-c]imidazole (21a) and the 6,7,8,9-tetrahydroimidazo[1,5-a]azepine (21b) analogues were synthesized and evaluated. CGS 16949 A's ability to selectively inhibit aromatase (IC50 = 4.5nM) over other cytochrome P-450 enzymes and suppress estrogen production when administered orally make it a suitable candidate to test the potential of an aromatase inhibitor in estrogen-dependent diseases including breast cancer.

  DOI：

  10.1021/jm00106a038

文献信息

• Selective C(8)–H Activation of Imidazopyridines Mediated by Cooperative Nickel–Aluminum Catalysis
  作者：Fu-Yu Tsai、Tiow-Gan Ong、Cheng-Yuan Liu、Ying-Ho Chen、Chih-Hao Chen、Ming-Shiuan Yu

  DOI：10.1055/s-0035-15661438

  日期：——

  This work is dedicated to the victims of the recent Tainan earthquake. Abstract A catalytic paradigm is described featuring a synergistic interaction between nickel, aluminum and different ligands to impart a rather remote C–H alkenylation of imidazo[1,5-a]pyridines at the C-8 position without the necessity of installing a directing group. The scope of the direct C–H activation reactions of various

  这项工作是针对最近台南地震的受害者。 抽象的 描述了一种催化范例，其特征在于镍，铝和不同配体之间具有协同相互作用，可在C-8位上使咪唑并[1,5- a ]吡啶具有相当远的CH链烯基化作用，而无需安装引导基团。使用不同的位阻炔烃确定各种5-芳基-和3-芳基偶氮吡啶的直接CH活化反应的范围。 描述了一种催化范例，其特征在于镍，铝和不同配体之间具有协同相互作用，可在C-8位上使咪唑并[1,5- a ]吡啶具有相当远的CH链烯基化作用，而无需安装引导基团。使用不同的位阻炔烃确定各种5-芳基-和3-芳基偶氮吡啶的直接CH活化反应的范围。
• Certain imidazo(1,5-a)pyridine derivatives and their use as thromboxane
  申请人：Ciba-Geigy Corporation

  公开号：US04588732A1

  公开（公告）日：1986-05-13

  Disclosed are compounds of the formula I ##STR1## or a 5,6,7,8-tetrahydro derivative thereof, wherein R.sub.1 is hydrogen, halogen, lower alkyl, lower alkoxy, hydroxy, or aryl-lower alkoxy in which aryl represents phenyl or phenyl substituted by lower alkoxy, lower alkyl, halogen or trifluoromethyl; R.sub.2 represents hydrogen, halogen, or lower alkyl; C represents carboxy, lower alkoxycarbonyl, unsubstituted or mono- or di-(lower alkyl) substituted carbamoyl, cyano, formyl, hydroxymethyl, 5-tetrazolyl, dihydro-2-oxazolyl, dihydro-2-oxazolyl substituted by lower alkyl, or hydroxycarbamoyl; and (a) A represents ethenylene or ethenylene substituted by lower alkyl; B is straight chain or branched alkylene of 1 to 12 carbon atoms, alkynylene or alkenylene of 2 to 12 carbon atoms, phenylene-lower alkylene, phenylene-lower alkenylene, phenylene, or phenylene-(thio or oxy)-lower alkylene; or (b) A represents a direct bond; B represents lower alkylenephenylene, phenylene lower alkylene, phenylene, lower alkylene-(thio or oxy)-lower alkylene, lower alkylene-(thio or oxy)-phenylene, phenylene-(thio or oxy)-lower alkylene, phenylene-lower alkenylene, lower alkylenephenylene-lower alkenylene, or straight chain or branched alkadienylene of 5 to 12 carbon atoms; or a pharmaceutically acceptable salt thereof; and methods of synthesis thereof. Said compounds are useful as selective thromboxane synthetase inhibitors for the treatment of diseases such as cerebral ischaemia, shock, thrombosis and ischaemic heart disease.

  本公开了化合物的结构如下：##STR1##或其5,6,7,8-四氢衍生物，其中R.sub.1为氢、卤素、低烷基、低烷氧基、羟基，或芳基-低烷氧基，其中芳基代表苯基或被低烷氧基、低烷基、卤素或三氟甲基取代的苯基；R.sub.2代表氢、卤素或低烷基；C代表羧基、低烷氧羰基、未取代或单取代或双取代（低烷基）的氨基甲酰基、氰基、甲酰基、羟甲基、5-四唑基、二氢-2-噁唑基、被低烷基取代的二氢-2-噁唑基，或羟基甲酰胺基；以及（a）A代表乙烯基或被低烷基取代的乙烯基；B为1至12个碳原子的直链或支链烷基、2至12个碳原子的炔基或烯基、苯基-低烷基、苯基-烯基、苯基，或苯基-(硫或氧)-低烷基；或（b）A代表直接键；B代表低烷基苯基、苯基低烷基、苯基、低烷基-(硫或氧)-低烷基、低烷基-(硫或氧)-苯基、苯基-(硫或氧)-低烷基、苯基-烯基、低烷基苯基-烯基、或5至12个碳原子的直链或支链烯二烯基；或其药学上可接受的盐；以及其合成方法。这些化合物可用作选择性血栓素合成酶抑制剂，用于治疗脑缺血、休克、血栓形成和缺血性心脏病等疾病。
• Substituted imidazo[5-a]pyridine derviatives and other substituted
  申请人：Ciba-Geigy Corporation

  公开号：US05428160A1

  公开（公告）日：1995-06-27

  Disclosed are compounds of formula I ##STR1## wherein R.sub.1 represents hydrogen, lower alkyl, substituted lower alkyl, nitro, halogen, free, etherified or esterified hydroxy, free, etherified, oxidised etherified or esterified mercapto, unsubstituted, mono- or disubstituted amino, ammonio, free or functionally modified sulfo, free or functionally modified formyl, C.sub.2 -C.sub.20 -acyl, cyano, free or functionally modified carboxy; and R.sub.2 represents hydrogen, lower alkyl, substituted lower alkyl, halogen; free, etherified or esterified hydroxy; free, etherified, oxidised etherified or esterified mercapto; free or functionally modified carboxy, or acyl; the 7,8-dihydro derivatives thereof; and compounds of the formula I* ##STR2## wherein n denotes 0, 1, 2, 3, or 4, and R.sub.1 and R.sub.2 are as defined above under formula I and salts thereof; e.g. as aromatase inhibitors; pharmaceutical compositions containing these compounds; the use of these compounds for the treatment of conditions responsive to e.g. aromatase inhibition in mammals; processes and intermediates for preparing these compounds.

  本发明涉及一种式子I的化合物：##STR1## 其中R.sub.1代表氢，低烷基，取代的低烷基，硝基，卤素，自由的，醚化或酯化的羟基，自由的，醚化，氧化醚化或酯化的巯基，未取代的，单取代或双取代的氨基，铵离子，自由的或功能修饰的磺酸基，自由的或功能修饰的甲酰基，C.sub.2-C.sub.20-酰基，氰基，自由的或功能修饰的羧基；R.sub.2代表氢，低烷基，取代的低烷基，卤素；自由的，醚化或酯化的羟基；自由的，醚化，氧化醚化或酯化的巯基；自由或功能修饰的羧基或酰基；其7,8-二氢衍生物；以及式I*的化合物：##STR2## 其中n表示0、1、2、3或4，而R.sub.1和R.sub.2如上述式I中所定义，并且它们的盐；例如作为芳香化酶抑制剂；含有这些化合物的制药组合物；这些化合物用于治疗响应于例如哺乳动物中的芳香化酶抑制的情况的用途；制备这些化合物的过程和中间体。
• Substituted imidazo[1,5-A]pyridine derivatives and other substituted
  申请人：Ciba-Geigy Corporation

  公开号：US04728645A1

  公开（公告）日：1988-03-01

  Disclosed are compounds of formula I ##STR1## wherein R.sub.1 represents hydrogen, lower alkyl, substituted lower alkyl, nitro, halogen, free, etherified or esterified hydroxy, free, etherified, oxidized etherified or esterified mercapto, unsubstituted, mono- or disubstituted amino, ammonio, free or functionally modified sulfo, free or functionally modified formyl, C.sub.2 -C.sub.20 -acyl, cyano, free or functionally modified carboxy; and R.sub.2 represents hydrogen, lower alkyl, substituted lower alkyl, halogen; free, etherified or esterified hydroxy; free, etherified, oxidized etherified or esterified mercapto; free or functionally modified carboxy, or acyl; the 7,8-dihydro derivatives thereof; and compounds of the formula I* ##STR2## wherein n denotes 0, 1, 2, 3 or 4, and R.sub.1 and R.sub.2 are as defined above under formula I and salts thereof; e.g. as aromatase inhibitors; pharmaceutical compositions containing these compounds; the use of these compounds for the treatment of conditions responsive to e.g. aromatase inhibition in mammals; processes and intermediates for preparing these compounds.

  本发明揭示了式I的化合物：##STR1## 其中R.sub.1代表氢、低碳基、取代的低碳基、硝基、卤素、自由、醚化或酯化的羟基、自由、醚化、氧化醚化或酯化的巯基、未取代的、单取代或双取代的氨基、铵离子、自由或功能修饰的磺酸基、自由或功能修饰的甲酰基、C.sub.2-C.sub.20酰基、氰基、自由或功能修饰的羧基；R.sub.2代表氢、低碳基、取代的低碳基、卤素；自由、醚化或酯化的羟基；自由、醚化、氧化醚化或酯化的巯基；自由或功能修饰的羧基或酰基。其7,8-二氢衍生物；以及式I*的化合物：##STR2## 其中n表示0、1、2、3或4，R.sub.1和R.sub.2如上所述，以及其盐；例如作为芳香化酶抑制剂；含有这些化合物的制药组合物；使用这些化合物治疗对哺乳动物的芳香化酶抑制等反应性疾病的方法；制备这些化合物的过程和中间体。
• Substituted imidazo[1,5-a]pyridine derivatives and other substituted
  申请人：Ciba-Geigy Corp.

  公开号：US04889861A1

  公开（公告）日：1989-12-26

  Disclosed are compounds of formula I ##STR1## wherein R.sub.1 represents hydrogen, lower alkyl, substituted lower alkyl, nitro, halogen, free, etherified or esterified hydroxy, free, etherified, oxidized etherified or esterified mercapto, unsubstituted, mono- or disubstituted amino, ammonio, free or functionally modified sulfo, free or functionally modified formyl, C.sub.2 --C.sub.20 -acyl, cyano, free or functionally modified carboxy; and R.sub.2 represents hydrogen, lower alkyl, substituted lower alkyl, halogen; free, etherified or esterified hydroxy; free, etherified, oxidized etherified or esterified mercapto; free or functionally modified carboxy, or acyl; the 7,8-dihydro derivatives thereof; and compounds of the formula I* ##STR2## wherein n denotes 0, 1, 2, 3 or 4, and R.sub.1 and R.sub.2 are as defined above under formula I and salts thereof; e.g. as aromatase inhibitors; pharmaceutical compositions containing these compounds; the use of these compounds for the treatment of conditions responsive to e.g. aromatase inhibition in mammals; processes and intermediates for preparing these compounds.

  本发明涉及式I的化合物，其中R.sub.1代表氢、低烷基、取代的低烷基、硝基、卤素、自由、醚化或酯化羟基、自由、醚化、氧化醚化或酯化巯基、未取代的、单取代或双取代的氨基、铵离子、自由或功能修饰的磺酸基、自由或功能修饰的甲酰基、C.sub.2-C.sub.20酰基、氰基、自由或功能修饰的羧基；R.sub.2代表氢、低烷基、取代的低烷基、卤素；自由、醚化或酯化羟基；自由、醚化、氧化醚化或酯化巯基；自由或功能修饰的羧基或酰基；其7,8-二氢衍生物；以及式I*的化合物，其中n表示0、1、2、3或4，R.sub.1和R.sub.2在式I下定义，以及它们的盐；例如作为芳香化酶抑制剂；含有这些化合物的制药组合物；这些化合物用于治疗哺乳动物对芳香化酶抑制等条件的用途；以及制备这些化合物的过程和中间体。