2-<4-(ethoxycarbonyl)phenyl>-6-<(formylamino)methyl>pyridine | 102676-41-5

• 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
• 英文名称: 2-<4-(ethoxycarbonyl)phenyl>-6-<(formylamino)methyl>pyridine
• 英文别名: 2-(p-ethoxycarbonylphenyl)-6-formylaminomethylpyridine；ethyl 4-[6-(formamidomethyl)pyridin-2-yl]benzoate
• CAS: 102676-41-5
• 化学式: C₁₆H₁₆N₂O₃
• 分子量: 284.315
• InChiKey: QKYILQOKUXDPHM-UHFFFAOYSA-N

物化性质

• 熔点：
  119.5-120.5 °C
• 沸点：
  504.6±50.0 °C(Predicted)
• 密度：
  1.178±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  68.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-<4-(ethoxycarbonyl)phenyl>-6-<(formylamino)methyl>pyridine 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 、 甲苯 为溶剂， 60.0~90.0 ℃ 、275.79 kPa 条件下， 反应 52.5h， 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 作用下， 以 甲醇 为溶剂， 90.0 ℃ 、101.33 kPa 条件下， 反应 42.0h， 生成 2-<4-(ethoxycarbonyl)phenyl>-6-<(formylamino)methyl>pyridine
  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

• 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[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。
• Substituierte bicyclische Verbindungen
  申请人：CIBA-GEIGY AG

  公开号：EP0165904B1

  公开（公告）日：1991-04-10
• BROWNE, LESLIE J.
  作者：BROWNE, LESLIE J.

  DOI：——

  日期：——
• BROWNE, L. J.;GUDE, C.;RODRIGUEZ, H.;STEELE, R. E.;BHATNAGER, A., J. MED. CHEM., 34,(1991) N, C. 725-736
  作者：BROWNE, L. J.、GUDE, C.、RODRIGUEZ, H.、STEELE, R. E.、BHATNAGER, A.

  DOI：——

  日期：——