2-(氯甲基)-4-苯基吡啶 | 147937-34-6

• 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: 2-(氯甲基)-4-苯基吡啶
• 英文名称: 2-(chloromethyl)4-phenyl-pyridine
• 英文别名: 4-phenyl-2-picolyl chloride；2-(Chloromethyl)-4-phenylpyridine
• CAS: 147937-34-6
• 化学式: C₁₂H₁₀ClN
• 分子量: 203.671
• InChiKey: JXQZTESQGQBTIV-UHFFFAOYSA-N

物化性质

• 沸点：
  313.1±27.0 °C(Predicted)
• 密度：
  1.159±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(氯甲基)-4-苯基吡啶 在 三甲基溴硅烷 作用下， 以 乙腈 为溶剂， 生成 (4-phenylpyridin-2-yl)methylphosphonic acid disodium salt
  参考文献：
  名称：

  Inhibition of 1-Deoxy-d-Xylulose-5-Phosphate Reductoisomerase by Lipophilic Phosphonates: SAR, QSAR, and Crystallographic Studies

  摘要：

  1-Deoxy-D-xylulose-5-phosphate reductoisomerase (DXR) is a novel target for developing new antibacterial (including antituberculosis) and antimalaria drugs. Forty-one lipophilic phosphonates, representing a new class of DXR inhibitors, were synthesized, among which 5-phenylpyridin-2-ylmethylphosphonic acid possesses the most activity against E. coli DXR (EcDXR) with a K-i of 420 nM. Structure-activity relationships (SAR) are discussed, which can be rationalized using our EcDXR:inhibitor structures, and a predictive quantitative SAR (QSAR) model is also developed. Since inhibition studies of DXR from Mycobacterium tuberculosis (MtDXR) have not been performed well, 48 EcDXR inhibitors with a broad chemical diversity were found, however, to generally exhibit considerably reduced activity against MtDXR. The crystal structure of a, MtDXR:inhibitor complex reveals the flexible loop containing the residues 198-208 has no strong interactions with the 3,4-dichlorophenyl group of the inhibitor, representing a structural basis for the reduced activity. Overall, these results provide implications in the future design and development of potent DXR inhibitors.

  DOI：

  10.1021/jm200363d
• 作为产物：
  描述：

  (4-苯基吡啶-2-基)甲醇 在 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 生成 2-(氯甲基)-4-苯基吡啶
  参考文献：
  名称：

  Inhibition of 1-Deoxy-d-Xylulose-5-Phosphate Reductoisomerase by Lipophilic Phosphonates: SAR, QSAR, and Crystallographic Studies

  摘要：

  1-Deoxy-D-xylulose-5-phosphate reductoisomerase (DXR) is a novel target for developing new antibacterial (including antituberculosis) and antimalaria drugs. Forty-one lipophilic phosphonates, representing a new class of DXR inhibitors, were synthesized, among which 5-phenylpyridin-2-ylmethylphosphonic acid possesses the most activity against E. coli DXR (EcDXR) with a K-i of 420 nM. Structure-activity relationships (SAR) are discussed, which can be rationalized using our EcDXR:inhibitor structures, and a predictive quantitative SAR (QSAR) model is also developed. Since inhibition studies of DXR from Mycobacterium tuberculosis (MtDXR) have not been performed well, 48 EcDXR inhibitors with a broad chemical diversity were found, however, to generally exhibit considerably reduced activity against MtDXR. The crystal structure of a, MtDXR:inhibitor complex reveals the flexible loop containing the residues 198-208 has no strong interactions with the 3,4-dichlorophenyl group of the inhibitor, representing a structural basis for the reduced activity. Overall, these results provide implications in the future design and development of potent DXR inhibitors.

  DOI：

  10.1021/jm200363d

文献信息

• Pyrimidine-thioalkyl and alkylether compounds
  申请人：PHARMACIA & UPJOHN COMPANY

  公开号：EP1247804A1

  公开（公告）日：2002-10-09

  The subject invention relates to pyrimidine-thioalkyl and alkylether compounds of Formula I and pyrimidine-thioalkyl and alkylethers of Formula IA, namely the compounds of Formula I where R4 is selected from the group consisting of -H or -NR15R16 where R15 is -H and R16 is -H, C1-C6 alkyl, -NH2 or R15 and R16 taken together with the -N form 1-pyrrolidino, 1-morpholino or 1-piperidino; and R6 is selected from the group consisting of -H, or halo (preferably -Cl); with the overall provisio that R4 and R6 are not both -H; The compounds of Formula IA are useful in the treatment of individuals who are HIV positive.

  该发明涉及Formula I的嘧啶硫代烷基和烷基醚化合物，以及Formula IA的嘧啶硫代烷基和烷基醚化合物，即Formula I中R4选自-H或-NR15R16的基团，其中R15为-H，R16为-H，C1-C6烷基，-NH2或R15和R16一起与-N形成1-吡咯啉基、1-吗啉基或1-哌啶基；以及R6选自-H或卤素（优选-Cl）的基团，总体规定是R4和R6不能同时为-H；Formula IA的化合物在治疗HIV阳性个体中是有用的。
• Pyridyl chroman
  申请人：Merck Patent Gesellschaft Mit Beschrankter Haftung

  公开号：US05767132A1

  公开（公告）日：1998-06-16

  Amino(thio)ether derivatives of formula I ##STR1## wherein R.sup.0, R.sup.1, R.sup.2, R.sup.3, R.sup.6, R.sup.7, R.sup.8, R.sup.9, X and Z are as defined herein, and their salts, are active on the central nervous system.

  式I的氨基（硫）醚衍生物，其中R.sup.0、R.sup.1、R.sup.2、R.sup.3、R.sup.6、R.sup.7、R.sup.8、R.sup.9、X和Z如本文所定义，并其盐，在中枢神经系统上具有活性。
• Thiopyrano (2,3,4-c,d) indoles as inhibitors of leukotriene biosynthesis
  申请人：MERCK FROSST CANADA INC.

  公开号：EP0518426A1

  公开（公告）日：1992-12-16

  Compounds having the formula I: are inhibitors of leukotriene biosynthesis. These compounds are useful as anti-asthmatic, anti-allergic, anti-inflammatory, and cytoprotective agents. They are also useful in treating angina, cerebral spasm, glomerular nephritis, hepatitis, endotoxemia, psoriasis, uveitis and allograft rejection and in preventing the formation of atherosclerotic plaques.

  具有式 I 的化合物： 是白三烯生物合成的抑制剂。这些化合物可用作抗哮喘、抗过敏、抗炎和细胞保护剂。它们还可用于治疗心绞痛、脑痉挛、肾小球肾炎、肝炎、内毒素血症、银屑病、葡萄膜炎和异体移植排斥反应，以及预防动脉粥样硬化斑块的形成。
• Amino(thio)ether derivatives as CNS active agents
  申请人：MERCK PATENT GmbH

  公开号：EP0707007A1

  公开（公告）日：1996-04-17

  Amino(thio)ether derivatives of formula I wherein R°, R¹, R², R³, R⁶, R⁷, R⁸, R⁹, X and Z are as defined in Claim 1, and their salts, are active on the central nervous system.

  式 I 的氨基（硫代）醚衍生物 其中 R°、R¹、R²、R³、R⁶、R⁷、R⁸、R⁹、X 和 Z 如权利要求 1 所定义，它们的盐类对中枢神经系统具有活性。
• 2-[5-(4-fluorophenyl)-3-pyridylmethylaminomethyl]chromane as CNS active agent
  申请人：MERCK PATENT GmbH

  公开号：EP1123933A1

  公开（公告）日：2001-08-16

  2-[5-(4-fluorophenyl)-3-pyridyl-methylaminomethyl]-chromane and its physiologically acceptable salts thereof and (S)-(+)-2-[5-(4-fluorophenyl)-3-pyridyl-methylaminomethyl]-chromane and its physiologically acceptable salts thereof are active on the central nervous system.

  2-[5-(4-氟苯基)-3-吡啶基-甲基氨基甲基]-色烷及其生理学上可接受的盐类和(S)-(+)-2-[5-(4-氟苯基)-3-吡啶基-甲基氨基甲基]-色烷及其生理学上可接受的盐类对中枢神经系统具有活性。