1-(3-cyanophenyl)-4-difluoromethyl-1H-1,2,3-triazole | 916151-06-9

• 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-cyanophenyl)-4-difluoromethyl-1H-1,2,3-triazole
• 英文别名: 3-[4-(Difluoromethyl)triazol-1-yl]benzonitrile
• CAS: 916151-06-9
• 化学式: C₁₀H₆F₂N₄
• 分子量: 220.181
• InChiKey: KYLNOZXQNBKYGK-UHFFFAOYSA-N

物化性质

• 熔点：
  119-120 °C
• 沸点：
  379.1±52.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  54.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(3-cyanophenyl)-4-difluoromethyl-1H-1,2,3-triazole 、 氨基硫脲 在 三氟乙酸 作用下， 反应 24.0h， 生成 5-(3-(4-(difluoromethyl)-1H-1,2,3-triazole-1-yl)phenyl)-1,3,4-thiadiazol-2-amine
  参考文献：
  名称：

  Novel 1,2,3-Triazole Derivatives for Use against Mycobacterium tuberculosis H37Rv (ATCC 27294) Strain

  摘要：

  The purpose of this study was to prepare various 4-substituted N-phenyl-1,2,3-triazole derivatives using click chemistry. The derivatives were screened in vitro for antimicrobial activity against Mycobacterium tuberculosis strain H37Rv (ATCC 27294) using the Alamar Blue susceptibility test. The activity was expressed as the minimum inhibitory concentration (MIC) in mu g/mL (mu M). Derivatives of isoniazid (INH), (E)-N'-[(1-aryl)-1H-1,2,3-triazole-4-yl)methylene] isonicotinoyl hydrazides, exhibited significant activity with MIC values ranging from 2.5 to 0.62 mu g/mL. In addition, they displayed low cytotoxicity against liver cells (hepatoma HepG2) and kidney cells (BGM), thereby providing a high therapeutic index. The results demonstrated the potential and importance of developing new INH derivatives to treat mycobacterial infections.

  DOI：

  10.1021/jm2003624
• 作为产物：
  描述：

  3-叠氮苯甲腈 在 copper(ll) sulfate pentahydrate 、 二甲氨基三氟化硫 、 sodium ascorbate 、 2-碘酰基苯甲酸 作用下， 以 二氯甲烷 、 水 、 二甲基亚砜 、 叔丁醇 为溶剂， 反应 24.0h， 生成 1-(3-cyanophenyl)-4-difluoromethyl-1H-1,2,3-triazole
  参考文献：
  名称：

  Novel 1,2,3-Triazole Derivatives for Use against Mycobacterium tuberculosis H37Rv (ATCC 27294) Strain

  摘要：

  The purpose of this study was to prepare various 4-substituted N-phenyl-1,2,3-triazole derivatives using click chemistry. The derivatives were screened in vitro for antimicrobial activity against Mycobacterium tuberculosis strain H37Rv (ATCC 27294) using the Alamar Blue susceptibility test. The activity was expressed as the minimum inhibitory concentration (MIC) in mu g/mL (mu M). Derivatives of isoniazid (INH), (E)-N'-[(1-aryl)-1H-1,2,3-triazole-4-yl)methylene] isonicotinoyl hydrazides, exhibited significant activity with MIC values ranging from 2.5 to 0.62 mu g/mL. In addition, they displayed low cytotoxicity against liver cells (hepatoma HepG2) and kidney cells (BGM), thereby providing a high therapeutic index. The results demonstrated the potential and importance of developing new INH derivatives to treat mycobacterial infections.

  DOI：

  10.1021/jm2003624

文献信息

• Synthesis, tuberculosis inhibitory activity, and SAR study of N-substituted-phenyl-1,2,3-triazole derivatives
  作者：Marilia S. Costa、Núbia Boechat、Érica A. Rangel、Fernando de C. da Silva、Alessandra M.T. de Souza、Carlos R. Rodrigues、Helena C. Castro、Ivan N. Junior、Maria Cristina S. Lourenço、Solange M.S.V. Wardell、Vitor F. Ferreira

  DOI：10.1016/j.bmc.2006.08.019

  日期：2006.12

  The aim of this work was to describe the synthesis, the in vitro anti-Mycobacterium tuberculosis profile, and the structure-activity relationship (SAR) study of new N-substituted-phenyl-1,2,3-triazole-4-carbaldehydes (3a-l). The reactions of aromatic amine hydrochlorides with diazomalonaldehyde (1) produced several N-substituted-phenyl-1,2,3-triazole-4-carbaldehydes (3a-l) in moderate-to-good yields

  这项工作的目的是描述新型N-取代的苯基-1,2,3-三唑-4-甲醛的合成，体外抗结核分枝杆菌谱以及结构-活性关系（SAR）研究（ 3a-1）。芳族胺盐酸盐与重氮丙二醛（1）的反应以中等至良好的产率产生了几种N-取代的苯基-1,2,3-三唑-4-甲醛（3a-1）。为了研究二氟亚甲基对这些化合物的抗分枝杆菌活性的影响，用DAST氟化三唑可将相应的甲醛化合物以优异的产率转化为新的二氟甲基衍生物（4a-1）。所有化合物的表征均通过分光光度法进行，另外1-（4-甲基苯基）-1,2,3-三唑-4-甲醛通过X射线晶体学测定。已经针对化合物对结核分枝杆菌H37Rv菌株（ATCC 27294）的抑制活性筛选了化合物（3a-1）和（4a-1），并且它们全部都能够抑制细菌的生长。有趣的是，与目前用于治疗结核病的药物相似，3a和3k的MIC值为2.5mug / mL表现出最好的抑制作用。我们的SAR研究表明，氢键
• AZOLE COMPOUNDS USED AS TUBERCULOSTATIC AND LEISHMANICIDE AGENTS
  申请人：Boechat Nubia

  公开号：US20090054501A1

  公开（公告）日：2009-02-26

  This invention refers to new 1,2,3-triazole and imidazole compounds included in the families of compounds represented by general formula VIII. where: X is an atom of “C” or “N;” where X is “N” the radicals do triazole ring are represented by: R 1 =COR 2 , CSR 3 , CN(R 4 )R 5 or CF 2 R 6 ; R 2 =H, NHNH 2 , alkyl, aryl substituted or not, OH, NR 7 R 8 or OR 9 ; R 3 =alkyl or aryl substituted or not; R 4 =H, OH, alkyl or aryl substituted or not; R 5 =R 6 =R 7 =R 8 =R 9 =R 10 =H, alkyl or aryl substituted or not; where X is “C” the radicals do imidazolic ring are represented by: R 1 =COR 2 ; R 2 =NHNH 2 , OH, OR 3 , or NR 4 R 5 ; R 3 =alkyl or aryl substituted or not; =R 5 H, alkyl or aryl substituted or not; R 10 =NHR 6 or NR 6 R 7 ; R 6 =R 7 =COR 8 ; R 8 =aryl substituted or not; while radical R n can be located in any one or in more than one of the carbon atoms of the aromatic ring, and these radicals can be equal or different, represented by hydrogen, alkylic groups with 1 or more carbon atoms in a linear or branched chain alkenes or alkynes, hydroxyl, hydroxyalkyl or oxygenated functions in acyclic or cyclic systems forming an heterocyclic ring, free or substituted amines, thioalkyl, donators and/or removing groupings of electrons or halogens, thus “n” can vary from 1 to 5. This invention also refers to a pharmaceutical composition comprising, as active principle, at least one of the azole compounds represented by the general formula VIII, to the use of such compositions and to method of treatment or inhibition de tuberculosis and leishmaniasis.

  本发明涉及新的1,2,3-三唑和咪唑化合物，这些化合物属于由通式VIII表示的化合物家族，其中：X是“C”或“N”的原子；当X为“N”时，三唑环的基团表示为：R1=COR2、CSR3、CN（R4）R5或CF2R6；R2=H、NHNH2、烷基、芳基取代或不取代、OH、NR7R8或OR9；R3=烷基或芳基取代或不取代；R4=H、OH、烷基或芳基取代或不取代；R5=R6=R7=R8=R9=R10=H、烷基或芳基取代或不取代；当X为“C”时，咪唑环的基团表示为：R1=COR2；R2=NHNH2、OH、OR3或NR4R5；R3=烷基或芳基取代或不取代；=R5H、烷基或芳基取代或不取代；R10=NHR6或NR6R7；R6=R7=COR8；R8=芳基取代或不取代；而基团Rn可以位于任何一个或多个芳香环的碳原子上，这些基团可以相等或不同，由氢、线性或支链烷基链上具有1个或多个碳原子的烷基基团、烯烃或炔烃、羟基、羟基烷基或在无环或环形系统中含氧杂环的功能、自由或取代的胺、硫代烷基、电子给体和/或电子受体基团或卤素表示，因此“n”可以从1到5变化。本发明还涉及一种制药组合物，其包含至少一种由通式VIII表示的唑类化合物作为活性成分，以及使用这种组合物的方法和治疗或抑制结核病和利什曼病的方法。
• US8436027B2
  申请人：——

  公开号：US8436027B2

  公开（公告）日：2013-05-07
• US8796316B2
  申请人：——

  公开号：US8796316B2

  公开（公告）日：2014-08-05
• [EN] AZOLE COMPOUNDS USED AS TUBERCULOSTATIC AND LEISHMANICIDE AGENTS<br/>[FR] COMPOSES DE TYPE AZOLE UTILISES EN TANT QU'AGENTS TUBERCULOSTATIQUES ET LEISHMANICIDES
  申请人：FUNDACAO OSWALDO CRUZ

  公开号：WO2007019660A2

  公开（公告）日：2007-02-22

  [EN] This invention refers to new 1, 2, 3-triazole and imidazole compounds included in the families of compounds represented by general formula VIII (see formula VIII) where: X is an atom of "C" or "N"; where X is "N" the radicals do triazole ring are represented by: R₁ = COR₂, CSR₃, CN(R₄)R₅ or CF₂R₆; R₂ = H, NHNH₂, alkyl, aryl substituted or not, OH, NR₇R₈ or OR₉ ; R₃ = alkyl or aryl substituted or not; R₄ = H, OH, alkyl or aryl substituted or not; R₅ = R₆ = R₇ = R₈ = R₉ = R₁₀ = H, alkyl or aryl substituted or not; where X is "C" the radicals do imidazolic ring are represented by : R₁ = COR₂; R₂ = NHNH₂, OH, OR₃, or NR₄R₅; R₃ = alkyl or aryl substituted or not; R₄ = R₅ = H, alkyl or aryl substituted or not; R₁₀ = NHR₆ or NR₆R₇; R6 = R7 = COR₈; R8 = aryl substituted or not; while radical R_n can be located in any one or in more than one of the carbon atoms of the aromatic ring, and these radicals can be equal or different, represented by hydrogen, alkylic groups with 1 or more carbon atoms in a linear or branched chain alkenes or alkynes, hydroxyl, hydroxyalkyl or oxygenated functions in acyclic or cyclic systems forming an heterocyclic ring, free or substituted amines, thioalkyl, donators and/or removing groupings of electrons or halogens, thus "n" can vary from 1 to 5. This invention also refers to a pharmaceutical composition comprising, as active principle, at least one of the azole compounds represented by the general formula VIII, to the use of such compositions and to method of treatment or inhibition de tuberculosis and leishmaniasis.
  [FR] L'invention concerne de nouveaux composés de 1, 2, 3-triazole et d'imidazole inclus dans les familles de composés représentés par la formule générale VIII, dans laquelle : X représente un atome de "C" ou "N" ; dans laquelle X représente "N" les radicaux du cycle triazole sont représentés par : R₁ = COR₂, CSR₃, CN(R₄)R₅ ou CF₂R₆; R₂ = H, NHNH₂, alkyle, aryle substitué ou non, OH, NR₇R₈ ou OR₉ ; R₃ = alkyle ou aryle substitué ou non ; R₄ = H, OH, alkyle ou aryle substitué ou non ; R₅ = R₆ = R₇ = R₈ = R₉ = R₁₀ = H, alkyle ou aryle substitué ou non ; dans laquelle X représente "C", les radicaux du cycle imidazolique sont représentés par : R₁ = COR₂; R₂ = NHNH₂, OH, OR₃, ou NR₄R₅; R₃ = alkyle ou aryle substitué ou non ; R₄ = R₅ = H, alkyle ou aryle substitué ou non ; R₁₀ = NHR₆ ou NR₆R₇ ; R6 = R7 = COR₈ ; R8 = aryle substitué ou non ; tandis que le radical R_n peut être situé dans n'importe lequel ou dans plus d'un des atomes de carbone du cycle aromatique, et lesdits radicaux peuvent être égaux ou différents, représentés par hydrogène, des groupes alkyliques à 1 atome de carbone ou plus dans une chaîne linéaire ou ramifiée d'alcènes ou d'alcynes, hydroxyle, hydroxyalkyle ou des fonctions oxygénées dans des systèmes acycliques ou cycliques formant un cycle hétérocyclique, des amines libres ou substituées, du thioalkyle, des donneurs et/ou supprimant des groupements d'électrons ou d'halogènes, ainsi "n" peut varier entre 1 et 5. L'invention concerne également une composition pharmaceutique comprenant, en tant que principe actif, au moins un des composés de type azole représentés par la formule générale VIII, ainsi que l'utilisation desdites compositions et un procédé de traitement ou d'inhibition de la tuberculose et de la leishmaniose.