methyl 3-cyano-2-vinyl-1-naphthoate | 263862-45-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: methyl 3-cyano-2-vinyl-1-naphthoate
• 英文别名: Methyl 3-cyano-2-ethenylnaphthalene-1-carboxylate
• CAS: 263862-45-9
• 化学式: C₁₅H₁₁NO₂
• 分子量: 237.258
• InChiKey: NWMMWPQJGPGUSR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 3-cyano-2-vinyl-1-naphthoate 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 以89%的产率得到3-氰基-2-乙基-1-萘甲酸甲酯
  参考文献：
  名称：

  Structural Analysis and Optimization of NK₁ Receptor Antagonists through Modulation of Atropisomer Interconversion Properties

  摘要：

  We have previously described a series of antagonists that showed high potency and selectivity for the NK1 receptor. However, these compounds also had the undesirable property of existing as a mixture of interconverting rotational isomers. Here we show that alteration of the 2-naphthyl substituent can modulate the rate of isomer exchange. Comparisons of the NK1 receptor affinity for the various conformational. forms has facilitated the development of a detailed NK1 pharmacophore model.

  DOI：

  10.1021/jm030197g
• 作为产物：
  描述：

  2-甲氧基-3-氰基-1-萘酸甲酯 在 四(三苯基膦)钯 、 2,6-二叔丁基-4-甲基苯酚 、 碘 、 magnesium 、 三乙胺 、 lithium chloride 作用下， 以 1,4-二氧六环 、 乙醚 、 二氯甲烷 、 苯 为溶剂， 反应 4.5h， 生成 methyl 3-cyano-2-vinyl-1-naphthoate
  参考文献：
  名称：

  Structural Analysis and Optimization of NK₁ Receptor Antagonists through Modulation of Atropisomer Interconversion Properties

  摘要：

  We have previously described a series of antagonists that showed high potency and selectivity for the NK1 receptor. However, these compounds also had the undesirable property of existing as a mixture of interconverting rotational isomers. Here we show that alteration of the 2-naphthyl substituent can modulate the rate of isomer exchange. Comparisons of the NK1 receptor affinity for the various conformational. forms has facilitated the development of a detailed NK1 pharmacophore model.

  DOI：

  10.1021/jm030197g

文献信息

• [EN] NAPHTHALENECARBOXAMIDES AS TACHYKININ RECEPTOR ANTAGONISTS<br/>[FR] NAPHTALENE-CARBOXAMIDES UTILISES EN TANT QU'ANTAGONISTES DES RECEPTEURS DES TACHYKININES
  申请人：ZENECA LTD

  公开号：WO2000020389A1

  公开（公告）日：2000-04-13

  A compound having formula (I) wherein R1 is oxo, -ORa, -OC(=O)Rb; or (A); R2 is H; or R?1 is -ORc and R2 is -ORd; or R1 and R2¿ together form -O(CH¿2?)mO-; and any pharmaceutically-acceptable salt thereof along with their use in treating depression, anxiety, asthma, rheumatoid arthritis, Alzheimer's disease, cancer, schizophrenia, oedema, allergic rhinitis, inflammation, pain, gastrointestinal-hypermotility, anxiety, emesis, Huntington's disease, psychoses including depression, hypertension, migraine, bladder hypermotility, or urticaria, along with methods of making the compounds and pharmaceutical compositions containing the compounds.

  化合物式(I)的化合物，其中R1是氧代、-ORa、-OC（=O）Rb；或（A）；R2是H；或者R1是-ORc且R2是-ORd；或者R1和R2在一起形成-O（CH2）mO-；以及其任何药学上可接受的盐，用于治疗抑郁症、焦虑症、哮喘、类风湿性关节炎、阿尔茨海默病、癌症、精神分裂症、水肿、过敏性鼻炎、炎症、疼痛、胃肠过度运动、焦虑症、呕吐、亨廷顿病、包括抑郁症、高血压、偏头痛、膀胱过度运动或荨麻疹的方法，以及制备这些化合物和含有这些化合物的制药组合物。
• Naphthalenecarboxamides as tachykinin receptor antagonists
  申请人：AstraZeneca AB

  公开号：EP1433783A2

  公开（公告）日：2004-06-30

  A compound having the formula (I) wherein R1 is oxo, -ORa, -OC(=O)Rb; or (A); R2 is H; or R1 is -ORc and R2 is -ORd; or R1 and R2 together form -O(CH2)mO-; R3 is H or alkyl; R4, R5 and R6 are independently selected from hydroxy, cyano, nitro, trifluoromethoxy, trifluoromethyl, alkylsulfonyl, halo, alkoxy, alkyl, cyanoalkyl, alkenyl, alkynyl, carboxy, alkoxy-carbonyl, carbamoyl, alkylcarbamoyl, di-alkylcarbamoyl, alkanoyl, alkanoylamino, aminosulfonyl, and substituted alkyl; or R4 and R5 together form -OCH2O- or -OC(CH3)2O-; R6 may additionally be hydrogen; R7 is substituted phenyl; R8 is selected from hydrogen, hydroxy, alkoxy, alkanoyloxy, alkanoyl, alkoxycarbonyl, alkanoylamino, alkyl, carbamoyl, alkylcarbamoyl, and bis(alkyl)carbamoyl; Ra is hydrogen or alkyl; Rb is alkyl, aryl or arylalkyl; Rc and Rd are independently selected from alkyl; m is 2, 3, or 4; and X1 and X2 are independently H or halogen, wherein at least one of X1 and X2 are halogen; and any pharmaceutically-acceptable salt thereof along with their use in treating depression, anxiety, asthma, rheumatoid arthritis, Alzheimer's disease, cancer, schizophrenia, oedema, allergic rhinitis, inflammation, pain, gastrointestinal-hypermotility, anxiety, emesis, Huntington's disease, psychoses including depression, hypertension, migraine, bladder hypermotility, or urticaria, along with methods of making the compounds and pharmaceutical compositions containing the compounds.

  具有式 (I) 的化合物 其中 R1 是氧代、-ORa、-OC(=O)Rb；或 (A)； R2 是 H；或 R1 是-ORc，R2 是-ORd；或 R1 和 R2 共同形成-O(CH2)mO-； R3 是 H 或烷基；R4、R5 和 R6 独立选自羟基、氰基、硝基、三氟甲氧基、三氟甲基、烷基磺酰基、卤代、烷氧基、烷基、氰基烷基、烯基、炔基、羧基、烷氧基羰基、氨基甲酰基、烷基氨基甲酰基、二烷基氨基甲酰基、烷酰基、烷酰氨基、氨基磺酰基和取代烷基；或 R4 和 R5 共同形成 -OCH2O- 或 -OC(CH3)2O-；R6 还可以是氢；R7 是取代的苯基；R8 选自氢、羟基、烷氧基、烷酰氧基、烷酰基、烷氧羰基、烷酰氨基、烷基、氨基甲酰基、烷基氨基甲酰基和双(烷基)氨基甲酰基；Ra 是氢或烷基；Rb 是烷基、芳基或芳烷基；Rc 和 Rd 独立地选自烷基；m 是 2、3 或 4；以及 X1 和 X2 独立地是 H 或卤素，其中 X1 和 X2 中至少有一个是卤素；及其任何药学上可接受的盐，以及它们在治疗抑郁症、焦虑症、哮喘、类风湿性关节炎、阿尔茨海默病、癌症、精神分裂症、水肿、过敏性鼻炎、炎症、疼痛、胃肠道过度运动、焦虑症、呃逆、亨廷顿氏病、包括抑郁症在内的精神病、高血压、偏头痛、膀胱过度运动或荨麻疹中的用途，以及制造这些化合物和含有这些化合物的药物组合物的方法。
• NAPHTHALENECARBOXAMIDES AS TACHYKININ RECEPTOR ANTAGONISTS
  申请人：AstraZeneca AB

  公开号：EP1119551A1

  公开（公告）日：2001-08-01
• Structural Analysis and Optimization of NK₁ Receptor Antagonists through Modulation of Atropisomer Interconversion Properties
  作者：Jeffrey S. Albert、Cyrus Ohnmacht、Peter R. Bernstein、William L. Rumsey、David Aharony、Yun Alelyunas、Daniel J. Russell、William Potts、Scott A. Sherwood、Lihong Shen、Robert F. Dedinas、William E. Palmer、Keith Russell

  DOI：10.1021/jm030197g

  日期：2004.1.1

  We have previously described a series of antagonists that showed high potency and selectivity for the NK1 receptor. However, these compounds also had the undesirable property of existing as a mixture of interconverting rotational isomers. Here we show that alteration of the 2-naphthyl substituent can modulate the rate of isomer exchange. Comparisons of the NK1 receptor affinity for the various conformational. forms has facilitated the development of a detailed NK1 pharmacophore model.