5-(bromomethyl)-2-chlorobenzonitrile | 99613-64-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-(bromomethyl)-2-chlorobenzonitrile
• CAS: 99613-64-6
• 化学式: C₈H₅BrClN
• 分子量: 230.491
• InChiKey: YHKXYWAZCJAGKK-UHFFFAOYSA-N

物化性质

• 熔点：
  55-58 °C
• 沸点：
  312.1±27.0 °C(Predicted)
• 密度：
  1.63±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 危险类别：
  8
• 危险性防范说明：
  P264,P270,P271,P280,P303+P361+P353,P304+P340,P305+P351+P338,P310,P330,P331,P363,P403+P233,P501
• 危险品运输编号：
  3261
• 危险性描述：
  H302,H314
• 包装等级：
  II

反应信息

• 作为反应物：
  描述：

  5-(bromomethyl)-2-chlorobenzonitrile 在 caesium carbonate 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 生成 2-chloro-5-((5,6-dihydroxy-5-methyl-7-nitro-2,3,5,6-tetrahydro-1H-pyrrolo[1,2-a]imidazol-1-yl)methyl)benzonitrile
  参考文献：
  名称：

  Water bridges are essential to neonicotinoids: Insights from synthesis, bioassay and molecular modelling studies

  摘要：

  Water-bridged H-bonds have been observed in many cases of ligand-receptor recognitions. To explore the roles of water bridges in the binding of neonicotinoids with receptors, twenty-four neonicotinoid compounds with nine fragments, including 1H-1,2,3-triazole, CN, COOMe, CONHNH2, CONHMe, NO2, NH2, NHCOMe and NHCSNH2 were synthesized and evaluated, of which, compounds with cyano group showed the best activities against Aphis craccivora. Accordingly, the cyano group is the optimal fragment mimicking the water bridge. Two cyano-substituted cis-nitromethylene compounds display good insecticidal activities, whereas the LC50 values are lower than those of their corresponding prototypes. Docking study showed that the cyano group acts only as H-bond acceptor, while the water bridge can act as both donor and acceptor. It revealed that the water bridge might be stable in the active site and was not suitable to be replaced by other groups. The findings illustrated that the water bridge is necessary for high insecticidal activities of neonicotinoids, which should be also helpful in better understanding the binding mode of neonicotinoids. (C) 2018 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.cclet.2018.05.013
• 作为产物：
  描述：

  间甲基苯腈 在 N-氯代丁二酰亚胺 、 N-溴代丁二酰亚胺(NBS) 、 palladium diacetate 、 对甲苯磺酸 、 过氧化苯甲酰 作用下， 以 四氯化碳 、 1,2-二氯乙烷 为溶剂， 生成 5-(bromomethyl)-2-chlorobenzonitrile
  参考文献：
  名称：

  Water bridges are essential to neonicotinoids: Insights from synthesis, bioassay and molecular modelling studies

  摘要：

  Water-bridged H-bonds have been observed in many cases of ligand-receptor recognitions. To explore the roles of water bridges in the binding of neonicotinoids with receptors, twenty-four neonicotinoid compounds with nine fragments, including 1H-1,2,3-triazole, CN, COOMe, CONHNH2, CONHMe, NO2, NH2, NHCOMe and NHCSNH2 were synthesized and evaluated, of which, compounds with cyano group showed the best activities against Aphis craccivora. Accordingly, the cyano group is the optimal fragment mimicking the water bridge. Two cyano-substituted cis-nitromethylene compounds display good insecticidal activities, whereas the LC50 values are lower than those of their corresponding prototypes. Docking study showed that the cyano group acts only as H-bond acceptor, while the water bridge can act as both donor and acceptor. It revealed that the water bridge might be stable in the active site and was not suitable to be replaced by other groups. The findings illustrated that the water bridge is necessary for high insecticidal activities of neonicotinoids, which should be also helpful in better understanding the binding mode of neonicotinoids. (C) 2018 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.cclet.2018.05.013

文献信息

• [EN] TRIAZOLE AND IMIDAZOLE DERIVATIVES FOR USE AS TGR5 AGONISTS IN THE TREATMENT OF DIABETES AND OBESITY<br/>[FR] DÉRIVÉS DE TRIAZOLE ET D'IMIDAZOLE DESTINÉS À ÊTRE UTILISÉS EN TANT QU'AGONISTES DE TGR5 DANS LE TRAITEMENT DU DIABÈTE ET DE L'OBÉSITÉ
  申请人：EXELIXIS INC

  公开号：WO2010093845A1

  公开（公告）日：2010-08-19

  The present invention comprises TGR5 agonists of structural formula I, wherein X, R1, R2, and R5 are defined herein, as well as N-oxides of them and pharmaceutically acceptable salts thereof. The invention further comprises composition comprising the compounds, N-oxides, and/or pharmaceutically acceptable salts thereof. The invention also comprises use of the compounds and compositions for treating diseases in which TGR5 is a mediator or is implicated. The invention also comprises use of the compounds in and for the manufacture of medicaments, particularly for treating diseases in which TGR5 is a mediator or is implicated.

  本发明包括结构式I的TGR5激动剂，其中X、R1、R2和R5在此处定义，以及它们的N-氧化物和其药学上可接受的盐。该发明还包括包含这些化合物、N-氧化物和/或其药学上可接受的盐的组合物。该发明还包括利用这些化合物和组合物治疗TGR5是介质或涉及的疾病。该发明还包括利用这些化合物制造药物，特别是用于治疗TGR5是介质或涉及的疾病。
• [EN] CAFFEINE INHIBITORS OF MTHFD2 AND USES THEREOF<br/>[FR] INHIBITEURS DE CAFÉINE DE MTHFD2 ET LEURS UTILISATIONS
  申请人：RAZE THERAPEUTICS INC

  公开号：WO2017106352A1

  公开（公告）日：2017-06-22

  The present invention provides compounds, compositions thereof, and methods of using the same.

  本发明提供了化合物、其组合物以及使用方法。
• [EN] 4 - PIPERIDINYL COMPOUNDS FOR USE AS TANKYRASE INHIBITORS<br/>[FR] COMPOSÉS DE 4-PIPÉRIDINYLE UTILES COMME INHIBITEURS DE LA TANKYRASE
  申请人：NOVARTIS AG

  公开号：WO2013008217A1

  公开（公告）日：2013-01-17

  The present invention provides for compounds of formula (I).The present invention also provides for pharmaceutical compositions and combinations comprising a compound of formula (I) as well as for the use of such compounds as tankyrase inhibitors and in the treatment of Wnt signaling and tankyrase 1 and 2 signaling related disorders which include, but are not limited to, cancer.

  本发明提供了化合物的结构式(I)。本发明还提供了包含结构式(I)化合物的药物组合物和组合物，以及利用这些化合物作为坦基酶抑制剂，并用于治疗Wnt信号和与坦基酶1和2信号相关的疾病，包括但不限于癌症。
• [EN] PURINE DERIVATIVES AND THEIR USE AS MODULATORS OF TOLL-LIKE RECEPTOR 7<br/>[FR] DÉRIVÉS DE PURINE ET LEUR UTILISATION COMME MODULATEURS DU RÉCEPTEUR DE TYPE TOLL-7
  申请人：GILEAD SCIENCES INC

  公开号：WO2009005687A1

  公开（公告）日：2009-01-08

  The present application includes purine compounds of Formula I or II: or a pharmaceutically acceptable salt, solvate, and/or ester thereof, compositions containing such compounds, therapeutic methods that include the administration of such compounds, and therapeutic methods that include the administration of such compounds with at least one additional active agent. Said compounds are used as modulators of Toll -like receptor 7.

  本申请包括式I或II的嘌呤化合物：或其药用可接受的盐、溶剂和/或酯，含有这些化合物的组合物，包括给予这些化合物的治疗方法，以及包括给予这些化合物和至少一种额外活性剂的治疗方法。所述化合物被用作调节Toll样受体7的调节剂。
• IMINOPYRIDINE DERIVATIVE AND USE THEREOF
  申请人：Takeda Pharmaceutical Company Limited

  公开号：EP2077262A1

  公开（公告）日：2009-07-08

  Provided are an iminopyridine derivative having a selective α1D adrenergic receptor antagonistic action and useful as an agent for the prophylaxis or treatment of a lower urinary tract disease and the like, and a screening method for a compound having an α1D adrenergic receptor antagonistic action. An α1D adrenergic receptor antagonist containing a compound represented by the formula: wherein each symbol is as defined in the specification, or a salt thereof, and a method of screening for an agent having an α1D adrenergic receptor antagonistic action for the prophylaxis or treatment of a lower urinary tract disease, which includes measuring the bladder smooth muscle tension of rats with bladder outlet obstruction.

  提供了一种具有选择性α1D肾上腺素能受体拮抗作用的咪唑吡啶衍生物，可用作预防或治疗下尿路疾病等药物，以及一种筛选具有α1D肾上腺素能受体拮抗作用的化合物的方法。该α1D肾上腺素能受体拮抗剂包含由下式表示的化合物或其盐：其中，每个符号如规范中所定义。该方法包括测量具有膀胱出口梗阻的大鼠膀胱平滑肌张力的药物，用于预防或治疗下尿路疾病的α1D肾上腺素能受体拮抗剂的筛选方法。