4-(3-溴苯基)-4H-1,2,4-三唑 | 375858-05-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 4-(3-溴苯基)-4H-1,2,4-三唑
• 中文别名: 4-(3-溴苯基)-1,2,4-三唑
• 英文名称: 4-(3-bromophenyl)-4H-1,2,4-triazole
• 英文别名: 4-(3-bromophenyl)-1,2,4-triazole
• CAS: 375858-05-2
• 化学式: C₈H₆BrN₃
• mdl: MFCD09971233
• 分子量: 224.06
• InChiKey: OZNSPEKVPJHTDF-UHFFFAOYSA-N

物化性质

• 沸点：
  353.5±44.0 °C(Predicted)
• 密度：
  1.63±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  30.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(3-溴苯基)-4H-1,2,4-三唑 、 5-(tri-n-butylstannyl)-3-phenyl pyridazine 在 四(三苯基膦)钯 作用下， 以 四氢呋喃 为溶剂， 反应 0.17h， 生成 3-phenyl-5-(3-[1,2,4] triazol-4-yl-phenyl)-pyridazine
  参考文献：
  名称：

  A New Pyridazine Series of GABA_A α5 Ligands

  摘要：

  Screening of the Merck compound collection identified 6 as an unusually simple, low molecular weight hit with moderate affinity for GABA(A) receptors. The structural novelty of 6, compared to our advanced series of GABA(A) alpha 5 inverse agonists, made it an attractive molecule for further exploration. This paper will describe the evolution of 6 into a new series of ligands with nanomolar affinity and functional selectivity for GABA(A) alpha 5 receptor subtypes.

  DOI：

  10.1021/jm050249x
• 作为产物：
  描述：

  N,N'-bis(dimethylaminomethylene)hydrazine 、 间溴苯胺 以 甲苯 为溶剂， 反应 4.0h， 以24.95%的产率得到4-(3-溴苯基)-4H-1,2,4-三唑
  参考文献：
  名称：

  WO2020112937A5

  摘要：

  公开号：

  WO2020112937A5

文献信息

• Discovery of (<i>S</i>)-3-(3-(3,5-Dimethyl-1<i>H</i>-pyrazol-1-yl)phenyl)-4-((<i>R</i>)-3-(2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethyl)pyrrolidin-1-yl)butanoic Acid, a Nonpeptidic α_vβ₆ Integrin Inhibitor for the Inhaled Treatment of Idiopathic Pulmonary Fibrosis
  作者：Panayiotis A. Procopiou、Niall A. Anderson、John Barrett、Tim N. Barrett、Matthew H. J. Crawford、Brendan J. Fallon、Ashley P. Hancock、Joelle Le、Seble Lemma、Richard P. Marshall、Josie Morrell、John M. Pritchard、James E. Rowedder、Paula Saklatvala、Robert J. Slack、Steven L. Sollis、Colin J. Suckling、Lee R. Thorp、Giovanni Vitulli、Simon J. F. Macdonald

  DOI：10.1021/acs.jmedchem.8b00959

  日期：2018.9.27

  the major product. A variety of aryl substituents including morpholine, pyrazole, triazole, imidazole, and cyclic ether were screened in cell adhesion assays for affinity against αvβ1, αvβ3, αvβ5, αvβ6, and αvβ8 integrins. Numerous analogs with high affinity and selectivity for the αvβ6 integrin were identified. The analog (S)-3-(3-(3,5-dimethyl-1H-pyrazol-1-yl)phenyl)-4-((R)-3-(2-(5,6,7,8-tetrahydro-1

  在（R）-BINAP存在下，通过铑催化的芳基硼酸的不对称1,4-加成反应，使用非对映选择性路线合成了一系列3-芳基（吡咯烷-1-基）丁酸主要产品的（S）绝对配置。包括吗啉，吡唑，三唑，咪唑，和环醚的各种芳基取代基中的细胞粘附试验中筛选针对α亲和力v β 1，α v β 3，α v β 5，α v β 6，α v β 8整联蛋白。具有高亲和力和选择性的α众多类似物v β 6整联进行鉴定。类似物（S）-3-（3-（3,5-二甲基-1 H-吡唑-1-基）苯基）-4-（（R）-3-（2-（5,6,7,8 -四氢-1,8-萘啶-2-基）乙基）吡咯烷-1-基）丁酸盐酸盐被发现具有为α非常高的亲和力v β 6整联在放射性配体结合测定（对ķ我= 11），较长的解离半衰期（7 h），在pH 7的盐水中具有很高的溶解度（> 71 mg / mL）和药代动力学特性，与通过雾化吸入给药相当。它被选作进一步的临床研
• [EN] PHENYLPYRIDAZINE DERIVATIVES AS LIGANDS FOR GABA RECEPTORS<br/>[FR] DERIVES DE PHENYLPYRIDAZINE UTILISES EN TANT QUE LIGANDS POUR DES RECEPTEURS GABA
  申请人：MERCK SHARP & DOHME

  公开号：WO2004014865A1

  公开（公告）日：2004-02-19

  A class of 4-phenylpyridazine derivatives of Formula (I), being selective ligands for GABAA receptors, in particular having high affinity for the α2 and/or α3 and or α5 subunit thereof, are accordingly of benefit in the treatment and/or prevention of adverse conditions of the central nervous system, including anxiety, convulsions and cognitive disorders.

  Formula (I)的4-苯基吡啶并衍生物是GABAA受体的选择性配体，特别是对其α2和/或α3和/或α5亚基具有高亲和力，因此在治疗和/或预防中枢神经系统的不良状况，包括焦虑、抽搐和认知障碍方面具有益处。
• [EN] NAPHTHYRIDINE DERIVATIVES AS ALPHA V BETA 6 INTEGRIN ANTAGONISTS FOR THE TREATMENT OF E.G. FIBROTIC DISEASES<br/>[FR] DÉRIVÉS DE NAPHTYRIDINE EN TANT QU'ANTAGONISTES DE L'INTÉGRINE ALPHA V BÊTA 6 POUR LE TRAITEMENT DE MALADIES FIBROTIQUES PAR EXEMPLE
  申请人：GLAXOSMITHKLINE IP DEV LTD

  公开号：WO2016046230A1

  公开（公告）日：2016-03-31

  A compound of formula (I) or a salt thereof wherein R1 represents a five-membered aromatic heterocycle selected from a N- or a C-linked mono- or di-substituted pyrazole, an N- or a C-linked optionally mono- or di-substituted triazole or an N- or a C-linked optionally mono-or di-substituted imidazole, which five-membered aromatic heterocycle may be substituted by one or two of the groups selected from a hydrogen atom, a methyl group, an ethyl group, a fluorine atom, a hydroxymethyl group, a 2-hydroxypropan-2-yl group, a trifluoromethyl group, a difluoromethyl group or a fluoromethyl group, except that when R1 represents an N-linked mono-or di-substituted pyrazole, R1 does not represent 3,5-Dimethyl-1H- pyrazol-1-yl, 5-Methyl-1H-pyrazol-1-yl, 5-Ethyl-3-methyl-1H-pyrazol-1-yl, 3,5-Diethyl-1H-pyrazol-1- yl, 4-Fluoro-3,5-dimethyl-1H-pyrazol-1-yl, 3-Methyl-1H- pyrazol-1-yl or 1H- pyrazol-1-yl.

  化合物的化学式（I）或其盐，其中R1代表从N-或C-连接的单取代或双取代吡唑、N-或C-连接的可选择单取代或双取代三唑或N-或C-连接的可选择单取代或双取代咪唑中选择的一种五元芳香杂环，该五元芳香杂环可以被氢原子、甲基、乙基、氟原子、羟甲基、2-羟基丙基、三氟甲基、二氟甲基或氟甲基中的一种或两种基团取代，但当R1代表N-连接的单取代或双取代吡唑时，R1不代表3,5-二甲基-1H-吡唑-1-基、5-甲基-1H-吡唑-1-基、5-乙基-3-甲基-1H-吡唑-1-基、3,5-二乙基-1H-吡唑-1-基、4-氟-3,5-二甲基-1H-吡唑-1-基、3-甲基-1H-吡唑-1-基或1H-吡唑-1-基。
• 3-Phenyl-imidazo-pyrimidine derivatives as ligands for gaba receptors
  申请人：——

  公开号：US20030176449A1

  公开（公告）日：2003-09-18

  A class of 3-phenylimidazo(1,2-&agr;) pyrimidine derivatives (of Formula I, or salt or prodrug thereof: I) wherein Y represents a chemical bond, an oxygen atom, or a —NH— linkage; Z represents an optionally substituted aryl or heteroaryl group; R 1 represents hydrogen, hydrocarbon, a heterocyclic group, halogen, cyano trifluoromethyl, nitro, —OR a , —SR a , —SOR a , —SO 2 R a , —SO 2 NR a R b , —NR a R b , —NR a COR b , —NR a CO 2 R b , —COR a , CO 2 R a , —CONR a R b or —CR a ═NOR b ; and R a and R b independently represent hydrogen, hydrocarbon or a heterocyclic group.), substituted at the meta position of the phenyl ring by an optionally substituted aryl or heteroaryl group which is directly attached or bridged by an oxygen atom or a —NH— linkage, are selective ligands for GABA A receptors, in particular having good affinity for the a2 and/or a3 and/or a5 subunit thereof, and are accordingly of benefit in the treatment and/or prevention of adverse conditions of the central nervous system, including anxiety, convulsions and cognitive disorders. 1

  一类3-苯基咪唑[1,2-a]嘧啶衍生物（化学式I，或其盐或前药：I），其中Y代表化学键，氧原子，或—NH—连接；Z代表可选择取代的芳基或杂芳基团；R1代表氢，碳氢化合物，杂环基团，卤素，氰基，三氟甲基，硝基，—ORa，—SRa，—SORa，—SO2Ra，—SO2NRaRb，—NRaRb，—NRaCORb，—NRaCO2Rb，—CORa，CO2Ra，—CONRaRb或—CRa═NORb；而Ra和Rb独立地代表氢，碳氢化合物或杂环基团，取代苯环的间位由一个可选择取代的芳基或杂芳基团取代，该芳基或杂芳基团直接连接或通过氧原子或—NH—连接桥接，是GABAA受体的选择性配体，特别对a2和/或a3和/或a5亚基具有良好的亲和力，因此对于治疗和/或预防中枢神经系统的不良症状，包括焦虑、抽搐和认知障碍具有益处。
• 3-Phenyl-imidazo-pyrimidine derivatives as ligands for GABA receptors
  申请人：Merck Sharp & Dohme Ltd.

  公开号：US06642229B2

  公开（公告）日：2003-11-04

  A class of 3-phenylimidazo(1,2-a)pyrimidine derivatives (of Formula I, or salt or prodrug thereof: I) wherein Y represents a chemical bond, an oxygen atom, or a —NH— linkage; Z represents an optionally substituted aryl or heteroaryl group; R1 represents hydrogen, hydrocarbon, a heterocyclic group, halogen, cyano trifluoromethyl, nitro, —ORa, —SRa, —SORa, —SO2Ra, —SO2NRaRb, —NRaRb, —NRaCORb, —NRaCO2Rb, —CORa, CO2Ra, —CONRaRb or —CRa═NORb; and Ra and Rb independently represent hydrogen, hydrocarbon or a heterocyclic group.), substituted at the meta position of the phenyl ring by an optionally substituted aryl or heteroaryl group which is directly attached or bridged by an oxygen atom or a —NH— linkage, are selective ligands for GABAA receptors, in particular having good affinity for the a2 and/or a3 and/or a5 subunit thereof, and are accordingly of benefit in the treatment and/or prevention of adverse conditions of the central nervous system, including anxiety, convulsions and cognitive disorders.

  一类3-苯基咪唑并[1,2-a]嘧啶衍生物（化学式I，或其盐或前药：I），其中Y代表化学键，氧原子或—NH—连接；Z代表可选取代的芳基或杂芳基基团；R1代表氢、碳氢化合物、杂环基团、卤素、氰、三氟甲基、硝基、—ORa、—SRa、—SORa、—SO2Ra、—SO2NRaRb、—NRaRb、—NRaCORb、—NRaCO2Rb、—CORa、CO2Ra、—CONRaRb或—CRa═NORb；而Ra和Rb分别独立地代表氢、碳氢化合物或杂环基团。这些衍生物在苯环的间位上取代了可选取代的芳基或杂芳基基团，该基团直接连接或通过氧原子或—NH—连接桥接，是GABAA受体的选择性配体，特别是对a2和/或a3和/或a5亚单位具有良好的亲和力，因此对于治疗和/或预防中枢神经系统的不良症状，包括焦虑、惊厥和认知障碍，具有益处。