2-苯基-2H-1,2,3,4-四唑-5-羧酸 | 54798-92-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 2-苯基-2H-1,2,3,4-四唑-5-羧酸
• 英文名称: 2-phenyl-2H-tetrazole-5-carboxylic acid
• 英文别名: 2-Phenyl-2H-tetrazol-5-carbonsaeure；2-Phenyltetrazol-5-carbonsaeure；2-phenyl-2H-tetrazole-5-carboxylic acid；2-Phenyl-2H-tetrazol-5-carbonsaeure；2-Phenyl-tetrazol-5-carbonsaeure；2-Phenyl-5-tetrazolcarbonsaeure；2H-Tetrazole-5-carboxylic acid, 2-phenyl-；2-phenyltetrazole-5-carboxylic acid
• CAS: 54798-92-4
• 化学式: C₈H₆N₄O₂
• mdl: MFCD03413881
• 分子量: 190.161
• InChiKey: YFIIOEOZTVRRDK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  80.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-苯基-2H-1,2,3,4-四唑-5-羧酸 在 五氯化磷 作用下， 以 吡啶 为溶剂， 反应 14.0h， 生成 1,4-Bis-(2-phenyl-2H-tetrazol-5-carboxy)benzen
  参考文献：
  名称：

  Csongar, Ch.; Weinberg, P.; Gessner, M., Journal fur praktische Chemie (Leipzig 1954), 1987, vol. 329, # 6, p. 1111 - 1115

  摘要：

  DOI：
• 作为产物：
  描述：

  (2E)-(苯基亚肼基)乙酸 在 2-azido-1,3,5-tribromobenzene 、 sodium 作用下， 以 乙醇 为溶剂， 反应 5.0h， 生成 2-苯基-2H-1,2,3,4-四唑-5-羧酸
  参考文献：
  名称：

  Synthesis and Structure−activity Relationships of Antitubercular 2-Nitroimidazooxazines Bearing Heterocyclic Side Chains

  摘要：

  Recently described biphenyl analogues Of the antituberculosis drug PA-824 displayed improved potencies against M. tuberculosis but were poorly soluble. Heterobiaryl analogues of these, in which the first phenyl ring was replaced with various 5-membered ring heterocycles, were prepared with the aim of identifying potent new candidates with improved aqueous solubility. The compounds were constructed by coupling the chiral 2-nitroimidazooxazine alcohol with various halomethyl-substituted arylheterocycles, by cycloadditions to a propargyl ether derivative of this alcohol, or by Suzuki couplings on haloheterocyclic methyl ether derivatives. The arylheterocyclic compounds were all more hydrophilic than their corresponding biphenyl analogues, and several showed solubility improvements. 1-Methylpyrazole, 1,3-linked-pyrazole, 2,4-linked-triazole, and tetrazole analogues had 3- to 7-fold higher MIC potencies against replicating M. tb than predicted by their lipophilicities. Two pyrazole analogues were >10-fold more efficacious than the parent drug in a mouse model of acute M. tb infection, and one displayed a 2-fold higher solubility.

  DOI：

  10.1021/jm901378u

文献信息

• [EN] PIPERAZINE DERIVATIVES AND THEIR USE AS POSITIVE ALLOSTERIC MODULATORS OF MGLU5 RECEPTORS<br/>[FR] DÉRIVÉS DE PIPÉRAZINE ET LEUR UTILISATION À TITRE DE MODULATEURS ALLOSTÉRIQUES POSITIFS DES RÉCEPTEURS MGLUR5
  申请人：BOEHRINGER INGELHEIM INT

  公开号：WO2013087805A1

  公开（公告）日：2013-06-20

  This invention relates to compounds of formula (I) their use as positive allosteric modulators of mGlu5 receptor activity, pharmaceutical compositions containing the same, and methods of using the same as agents for treatment and/or prevention of neurological and psychiatric disorders associated with glutamate dysfunction such as schizophrenia or cognitive decline such as dementia or cognitive impairment. R1, R2, R3, R4, Q have meanings given in the description.

  这项发明涉及公式(I)化合物，它们作为mGlu5受体活性的正向变构调节剂的用途，含有这些化合物的药物组合物，以及将其用作治疗和/或预防与谷氨酸功能障碍相关的神经和精神障碍，如精神分裂症或认知功能下降，如痴呆症或认知障碍的药剂的方法。R1、R2、R3、R4、Q在描述中有给定的含义。
• NOVEL COMPOUNDS
  申请人：HEIMANN Annekatrin

  公开号：US20130158042A1

  公开（公告）日：2013-06-20

  This invention relates to compounds of formula I their use as positive allosteric modulators of mGlu5 receptor activity, pharmaceutical compositions containing the same, and methods of using the same as agents for treatment and/or prevention of neurological and psychiatric disorders associated with glutamate dysfunction such as schizophrenia or cognitive decline such as dementia or cognitive impairment. R 1 , R 2 , R 3 , R 4 , Q have meanings given in the description.

  这项发明涉及公式I的化合物，它们作为mGlu5受体活性的正向变构调节剂的用途，含有这些化合物的药物组合物，以及将其用作治疗和/或预防与谷氨酸功能障碍相关的神经和精神障碍，如精神分裂症或认知功能下降，如痴呆症或认知障碍的药剂的方法。R1，R2，R3，R4，Q在描述中给出了含义。
• CXCR7 ANTAGONISTS
  申请人：ChemoCentryx, Inc.

  公开号：US20140154179A1

  公开（公告）日：2014-06-05

  Compounds having formula I, or pharmaceutically acceptable salts, hydrates or N-oxides thereof are provided and are useful for binding to CXCR7, and treating diseases that are dependent, at least in part, on CXCR7 activity. Accordingly, the present invention provides in further aspects, compositions containing one or more of the above-noted compounds in admixture with a pharmaceutically acceptable excipient.

  提供具有化学式I的化合物，或其药用可接受的盐、水合物或N-氧化物，并且这些化合物可用于与CXCR7结合，治疗部分或完全依赖于CXCR7活性的疾病。因此，根据本发明的进一步方面，提供含有上述化合物之一或多个的组合物与药用可接受的赋形剂混合物。
• Preparation of 2-(2<i>H</i>-Tetrazol-2-yl)benzoic Acids via Regioselective Cu(I) Catalyzed N2 Arylation of Tetrazole
  作者：Zhiguo Jake Song、Peter Maligres、Carmela Molinaro、Guy Humphrey、Jeff Fritzen、Jonathan Wilson、Yonggang Chen

  DOI：10.1021/acs.oprd.9b00243

  日期：2019.11.15

  2-(2H-Tetrazol-2-yl)benzoic acid 1 and analogs were prepared via Cu(I) catalyzed C–N coupling of 2-iodo or 2-bromo benzoic acids with 5-(ethylthio)-1H-tetrazole followed by reductive cleavage of the thioether bond. The C–N coupling was regioselective toward the N2-position on tetrazole. The scope of this methodology was demonstrated on a series of 2-halobenzoic acid substrates in moderate yields.

  2-（2 H-替他唑-2-基）苯甲酸1及其类似物是通过Cu（I）催化2-碘或2-溴苯甲酸与5-（乙硫基）-1 H-四唑的C–N偶联制备的然后还原性裂解硫醚键。C–N偶联对四唑的N2-位置具有区域选择性。在一系列2-卤代苯甲酸底物上以中等收率证明了该方法的范围。
• Genetically Encoded 2-Aryl-5-carboxytetrazoles for Site-Selective Protein Photo-Cross-Linking
  作者：Yulin Tian、Marco Paolo Jacinto、Yu Zeng、Zhipeng Yu、Jun Qu、Wenshe R. Liu、Qing Lin

  DOI：10.1021/jacs.7b02615

  日期：2017.5.3

  reactivity in E. coli when placed at an appropriate site at the protein interaction interface. A comparison study indicated that mPyTK exhibits higher photo-cross-linking efficiency than a diazirine-based photo-cross-linker, AbK, when placed at the same location of the interaction interface in vitro. When mPyTK was introduced into the adapter protein Grb2, it enabled the photocapture of EGFR in a stimulus-dependent

  遗传编码的光交联剂有望提供一个时间控制的工具，以绘制活细胞中瞬时和动态的蛋白质-蛋白质相互作用复合物。在这里我们报告了2-芳基-5-羧基四唑-赖氨酸类似物（ACTKs）的合成及其通过大肠杆菌和哺乳动物细胞中的琥珀色密码子抑制将它们的位点特异性掺入蛋白质中。在研究的五种ACTK中，发现N-甲基吡咯四唑-赖氨酸（mPyTK）在大肠杆菌中具有强大的位点选择性光交联反应性。当放置在蛋白质相互作用界面的适当位置时。一项比较研究表明，当在体外将mPyTK放置在相互作用界面的相同位置时，其显示出的光交联效率要高于基于二嗪胺的光交联剂AbK。当将mPyTK引入衔接蛋白Grb2中时，它能够以刺激依赖的方式实现EGFR的光捕获。mPyTK的设计及其同源氨基酰-tRNA合成酶的鉴定，使得可以绘制瞬时蛋白与蛋白的相互作用及其在活细胞中的界面。

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