1-(3-chloro-4-fluorophenyl)-1H-1,2,3,4-tetrazole | 351373-03-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(3-chloro-4-fluorophenyl)-1H-1,2,3,4-tetrazole
• 英文别名: 1-(3-chloro-4-fluorophenyl)-1H-tetrazole；1-(3-chloro-4-fluorophenyl)tetrazole
• CAS: 351373-03-0
• 化学式: C₇H₄ClFN₄
• 分子量: 198.587
• InChiKey: JDVFKEIDWJLVTM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  13
• 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：
  43.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(3-chloro-4-fluorophenyl)-1H-1,2,3,4-tetrazole 在 氢氧化钾 、 二甲基亚砜 作用下， 以 乙醇 为溶剂， 以87%的产率得到3-chloro-4-fluorophenylcyanamide
  参考文献：
  名称：

  Synthesis of New Functionally Substituted 1-R-tetrazoles and Their 5-Amino Derivatives

  摘要：

  DOI：

  10.1007/s10593-005-0267-4
• 作为产物：
  描述：

  3-氯-4-氟苯甲醛 在 sodium azide 作用下， 以 甲醇 为溶剂， 反应 5.0h， 以87%的产率得到1-(3-chloro-4-fluorophenyl)-1H-1,2,3,4-tetrazole
  参考文献：
  名称：

  通过基于异氰酸酯的[3 + 2]环加成反应，由醛在可见光下驱动的区域选择性合成1 H-四唑

  摘要：

  报道了新颖的和绿色的Co @ gC 3 N 4催化可见光驱动的直接由各种醛和叠氮化钠直接区域选择性合成1 H-四唑。在此，NaN 3不仅起到四唑环的三氮供体的作用，而且还将醛转化成作为一氮源的异氰酸酯。产品的区域选择性，操作简便，环境反应条件，不使用柱色谱法进行纯化，优异的产品收率（84–95％）和催化剂的可回收性高达五倍，而形态和催化效率没有任何实质性变化是所设想协议的显着特征。

  DOI：

  10.1039/c8gc01321g

文献信息

• One-Pot Syntheses of 5-Amino-1-aryltetrazole Derivatives
  作者：Andrey Vorobiov、Pavel Gaponik、Petr Petrov、Oleg Ivashkevich

  DOI：10.1055/s-2006-926403

  日期：2006.4

  A novel facile route for the introduction of 5-amino and 5-alkylamino substituents into 1-aryltetrazoles has been developed. A range of 5-amino-1-aryltetrazoles was obtained directly from the corresponding 1-aryltetrazoles in one pot by consecutive ring-opening, azidation and intramolecular cyclization. 5-Alkylamino-1-aryltetrazoles were formed by a similar mechanism from 1,4-disubstituted tetrazolium salts. An influence of the nature of aryl substituents and reaction conditions on the regioselectivity of the intramolecular cyclization of intermediate guanyl azides is revealed.

  已开发出一种新颖简便的方法，将5-氨基和5-烷基氨基取代基引入到1-芳基四唑中。通过连续的开环、叠氮化和分子内环化反应，从相应的1-芳基四唑一锅获得了一系列5-氨基-1-芳基四唑。5-烷基氨基-1-芳基四唑是通过类似机制从1,4-二取代的四唑盐形成的。研究揭示了芳基取代基的性质和反应条件对中间体氨基叠氮盐分子内环化反应的区域选择性的影响。
• Sulfocoumarins as dual inhibitors of human carbonic anhydrase isoforms IX/XII and of human thioredoxin reductase
  作者：Mikhail Krasavin、Raivis Žalubovskis、Aiga Grandāne、Ilona Domračeva、Petr Zhmurov、Claudiu T. Supuran

  DOI：10.1080/14756366.2020.1712596

  日期：2020.1.1

  acting as inhibitors of human carbonic anhydrase (CA, EC 4.2.1.1) cancer-associated isoforms hCA IX and - hCA XII is being able to also inhibit thioredoxin reductase was verified and confirmed. The dual targeting of two cancer cell defence mechanisms, i.e. hypoxia and oxidative stress, may both contribute to the observed antiproliferative profile of these compounds against many cancer cell lines. This

  证实并证实了硫代香豆素可作为人类碳酸酐酶抑制剂（CA，EC 4.2.1.1）与癌症相关的亚型hCA IX和-hCA XII的抑制剂也能抑制硫氧还蛋白还原酶的假说。两种癌细胞防御机制（即缺氧和氧化应激）的双重靶向可能都有助于观察到的这些化合物对多种癌细胞的抗增殖作用。这种前所未有的双重抗癌机制可能会导致设计创新治疗剂的新方法。
• Efficient and rapid synthesis of 1-substituted-1H-1,2,3,4-tetrazoles in the acidic ionic liquid 1-n-butylimidazolium tetrafluoroborate
  作者：Taterao M. Potewar、Shafi A. Siddiqui、Rajgopal J. Lahoti、Kumar V. Srinivasan

  DOI：10.1016/j.tetlet.2007.01.050

  日期：2007.3

  An efficient synthesis leading directly to 1-substituted-1H-1,2,3,4-tetrazoles from easily available amines and sodium azide in stoichiometric proportions using a room-temperature ionic liquid, namely, 1-n-butylimidazolium tetrafluoroborate in excellent yields is described. The inherent Bronsted acidity and high polarity of the IL results in a significant enhancement in the reaction rate. (c) 2007 Elsevier Ltd. All rights reserved.
• A novel synthesis of 1-aryl tetrazoles promoted by employing the synergy of the combined use of DMSO and an ionic liquid as the solvent system at ambient temperature
  作者：Satish N. Dighe、Kishor S. Jain、Kumar V. Srinivasan

  DOI：10.1016/j.tetlet.2009.08.063

  日期：2009.11

  The synergy of the combined use of DMSO and an ionic liquid viz. (bbim)*Br- has brought about a mild, convenient, efficient, and rapid protocol for the synthesis of 1-substituted-1H-1,2,3,4-tetrazoles via the condensation of amines, triethyl orthoformate, and sodium azide at ambient temperature in excellent isolated yields (85-90%). The inherent Bronsted acidity of ionic liquid and high polarity of both IL and DMSO resulted in a significant enhancement in the reaction rate. (C) 2009 Elsevier Ltd. All rights reserved.
• Synthesis of 6-tetrazolyl-substituted sulfocoumarins acting as highly potent and selective inhibitors of the tumor-associated carbonic anhydrase isoforms IX and XII
  作者：Aiga Grandane、Muhammet Tanc、Raivis Zalubovskis、Claudiu T. Supuran

  DOI：10.1016/j.bmc.2014.01.043

  日期：2014.3

  A series of 6-substituted sulfocoumarins incorporating substituted-1,2,3,4-tetrazol-5-yl moieties were synthesized by reaction of 6-iodo-sulfocoumarin and the corresponding tetrazole via the CH activation reaction. The new sulfocoumarins incorporating alkyl and substituted aryl moieties at the 1-position of the tetrazole, were investigated for the inhibition of four human (h) carbonic anhydrase (hCA, EC 4.2.1.1) isoforms, the cytosolic hCA I and II; and the transmembrane, tumor-associated hCA IX and XII. The tetrazole-substituted sulfocoumarins did not inhibit the ubiquitous, off-target cytosolic isoforms (K(I)s > 10 mu M) but showed effective inhibition against the two transmembrane CAs, with KIs ranging from 6.5 to 68.6 nM against hCA IX, and between 4.3 and 59.8 nM against hCA XII. As hCA IX and XII are validated anti-tumor targets, such prodrug, isoform-selective inhibitors as the sulfocoumarins reported here, may be useful for identifying suitable drug candidates for clinical trials. (C) 2014 Elsevier Ltd. All rights reserved.