4-(2-[1,2,4]triazol-1-ylacetyl)benzonitrile | 103962-24-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(2-[1,2,4]triazol-1-ylacetyl)benzonitrile
• 英文别名: 4-(1,2,4-triazol-1-ylacetyl)benzonitrile；4-cyano-alpha-(1,2,4-triazol-1-yl)acetophenone；4-[(1H-1,2,4-Triazol-1-yl)acetyl]benzonitrile；4-[2-(1,2,4-triazol-1-yl)acetyl]benzonitrile
• CAS: 103962-24-9
• 化学式: C₁₁H₈N₄O
• 分子量: 212.211
• InChiKey: HESQOOGWZWYVSZ-UHFFFAOYSA-N

物化性质

• 沸点：
  485.7±55.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  71.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(2-[1,2,4]triazol-1-ylacetyl)benzonitrile 在 potassium carbonate 、 Selectfluor 作用下， 以 乙腈 为溶剂， 反应 22.0h， 以37%的产率得到4-[2-fluoro-2-(1,2,4-triazol-1-yl)acetyl]benzonitrile
  参考文献：
  名称：

  JP2015/848

  摘要：

  公开号：
• 作为产物：
  描述：

  对氰基苯乙酮 在 溴 、 sodium hydride 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 0.75h， 生成 4-(2-[1,2,4]triazol-1-ylacetyl)benzonitrile
  参考文献：
  名称：

  Synthesis and antifungal activity of a series of novel 1,2-disubstituted propenones

  摘要：

  To find an antifungal agent other than those of the imidazole and triazole series, a new class of 1,2-disubstituted propenones I and II was prepared and tested for antifungal activity. Comparison of the structure-activity relationships showed that the conjugated structure of carbonyl and exomethylene groups in I and II plays an important role in potent antifungal activity. However, it is noteworthy that compounds 53, 54, and 56, which have a hydroxymethyl or methoxymethyl group instead of an exo-methylene group in I, also showed potent activity. Although many compounds exhibited strong antifungal activity in vitro, none showed activity in vivo of oral efficacy against subacute systemic candidiasis in mice.

  DOI：

  10.1021/jm00391a037

文献信息

• Synthesis, Binding Mode, and Antihyperglycemic Activity of Potent and Selective (5-Imidazol-2-yl-4-phenylpyrimidin-2-yl)[2-(2-pyridylamino)ethyl]amine Inhibitors of Glycogen Synthase Kinase 3
  作者：Allan S. Wagman、Rustum S. Boyce、Sean P. Brown、Eric Fang、Dane Goff、Johanna M. Jansen、Vincent P. Le、Barry H. Levine、Simon C. Ng、Zhi-Jie Ni、John M. Nuss、Keith B. Pfister、Savithri Ramurthy、Paul A. Renhowe、David B. Ring、Wei Shu、Sharadha Subramanian、Xiaohui A. Zhou、Cynthia M. Shafer、Stephen D. Harrison、Kirk W. Johnson、Dirksen E. Bussiere

  DOI：10.1021/acs.jmedchem.7b00922

  日期：2017.10.26

  -yl)[2-(2-pyridylamino)ethyl]amine analogues which are inhibitors of human glycogen synthase kinase 3 (GSK3). We developed efficient synthetic routes to explore a wide variety of substitution patterns and convergently access a diverse array of analogues. Compound 1 (CHIR-911, CT-99021, or CHIR-73911) emerged from an exploration of heterocycles at the C-5 position, phenyl groups at C-4, and a variety

  为了鉴定新的抗糖尿病药，我们发现了一种新型的（5-咪唑-2--2-基-4-苯基嘧啶-2-基）[2-（2-吡啶基氨基）乙基]胺类似物，它们是人类的抑制剂。糖原合酶激酶3（GSK3）。我们开发了有效的合成路线来探索各种取代模式，并会聚各种类似物。化合物1（CHIR-911，CT-99021或CHIR-73911）来自对C-5位置的杂环，C-4的苯基以及C处连接的各种不同取代的连接基和氨基吡啶部分的探索-2位置。这些化合物表现出GSK3 IC 50在低纳摩尔范围内和出色的选择性。它们激活表达胰岛素受体的CHO-IR细胞和原代大鼠肝细胞中的糖原合酶。在2型糖尿病的啮齿动物模型中对先导化合物1和2（CHIR-611或CT-98014）的评估表明，单次口服剂量可在60分钟内降低高血糖症，增强胰岛素刺激的葡萄糖转运，并改善葡萄糖的处置而不增加胰岛素水平。
• Antifugal azole compounds
  申请人：Imperial Chemical Industries PLC

  公开号：US04925863A1

  公开（公告）日：1990-05-15

  1,3-Diazolyl-2-propanol derivatives of the formula ##STR1## wherein X and Y are N or CH, R.sup.1 is phenyl, heterocyclyl, heterocyclyl-alkyl, -alkenyl or -alkynyl, optionally substituted, R.sup.2 and R.sup.3 are hydrogen or alkyl, and R.sup.4 and R.sup.5 are hydrogen, amino, alkoxyalkyl, aminoalkyl, alkylaminoalkyl, dialkylaminoalkyl, or alkenyl, or phenyl, phenylalkyl or phenylalkenyl, heterocycyl, heterocyclyalkyl or heterocyclylalkenyl, each optionally substituted, provided that when R.sup.1 is optionally substituted phenyl at least one of R.sup.1, R.sup.4 and R5 is, or contains, a phenyl ring bearing at least one substitutent selected from cyano, cyanoalkyl, nitro, aminocarbonylalkyl, halogeneoalkoxy and radicals of the formulae --CONR.sup.6 R.sup.7, --NHCOR.sup.8 or OR.sup.9 as defined herein, and the acid addition salts of compounds which contain a basic substituent; together with processes for their manufacture, pharmaceutical, veterinary and plant antifungal compositions, a method of treating fungal diseases in plants, and the use of the compounds for the manufacture of pharmacuetical or veterinary antifungal compositions.

  1,3-二唑基-2-丙醇衍生物的化学式为##STR1##其中X和Y为N或CH，R.sup.1为苯基，杂环烷基，杂环烷基-烷基，-烯基或-炔基，可选地取代，R.sup.2和R.sup.3为氢或烷基，R.sup.4和R.sup.5为氢，氨基，烷氧基烷基，氨基烷基，烷基氨基烷基，二烷基氨基烷基，或烯基，苯基，苯基烷基或苯基烯基，杂环基，杂环烷基或杂环烯基，每个可选地取代，但当R.sup.1为可选取代的苯基时，R.sup.1，R.sup.4和R5中至少一个是苯环，带有至少一种取代基，所述取代基选自氰基，氰基烷基，硝基，氨基羰基烷基，卤代烷氧基和所述处所定义的--CONR.sup.6 R.sup.7，--NHCOR.sup.8或OR.sup.9基团，以及含有碱性取代基的化合物的酸盐；以及其制备方法，制药，兽医和植物抗真菌组合物，治疗植物真菌病的方法，以及用于制备药用或兽医用抗真菌组合物的化合物的用途。
• Azole derivatives
  申请人：Imperial Chemical Industries PLC

  公开号：US04999364A1

  公开（公告）日：1991-03-12

  Azole derivatives of the formulas R.sup.1 --CR.sup.2 R.sup.3 --CHR.sup.4 --CR.sup.5 R.sup.6 --R.sup.7 are described; wherein R.sup.1 is a heterocyclyl radicla selected from 1,2,4-triazolyl, optionally-substituted imidazolyl, pyridyl and pyrimidinyl radicals; R.sup.2 and R.sup.3, which may be the same or different, are each a hydrogen atom or a 1-6C alkyl radical; R.sup.5 and R.sup.6, which may be the same or different, are each a hydrogen or fluorine atom or a 1-6C alkyl radical; one of R.sup.4 and R.sup.7 is a 2-pyridyl or 2-thienyl radical, optionally bearing one or more substituents selected from halogen atoms, cyano radicals and 1-4C halogenoalkyl and halogenoalkoxy radicals, and the other of R.sup.4 and R.sup.7 is a 4-cyanophenyl radical or a 2-pyridyl or 2-thienyl radical optionally substituted as defined above. Processes for their preparation are described, as is their use as aromatase inhibitors, for example in the treatment of cancer, as plant antifungal agents or as plant growth regulatory agents.

  本文描述了化合物的式子R.sup.1 --CR.sup.2 R.sup.3 --CHR.sup.4 --CR.sup.5 R.sup.6 --R.sup.7，其中R.sup.1是从1,2,4-三唑基，可选取代的咪唑基，吡啶基和嘧啶基中选择的杂环基；R.sup.2和R.sup.3，可以相同也可以不同，是氢原子或1-6C烷基基团；R.sup.5和R.sup.6，可以相同也可以不同，是氢原子或氟原子或1-6C烷基基团；R.sup.4和R.sup.7中的一个是2-吡啶基或2-噻吩基，可以带有一个或多个卤素原子，氰基和1-4C卤代烷基和卤代烷氧基，而R.sup.4和R.sup.7中的另一个是4-氰基苯基或2-吡啶基或2-噻吩基，可选按上述定义取代。本文还描述了它们的制备方法，以及它们作为芳香化酶抑制剂的用途，例如在癌症治疗中，作为植物抗真菌剂或植物生长调节剂。
• Antifungal azole compounds
  申请人：IMPERIAL CHEMICAL INDUSTRIES PLC

  公开号：EP0174769A1

  公开（公告）日：1986-03-19

  1,3-Diazolyl-2-propanol derivatives of the formula:- wherein X and Y are N or CH, R' is phenyl, heterocyclyl, heterocyclyl-alkyl, -alkenyl or - alkynyl, optionally substituted, R2 and R3 are hydrogen or alkyl, and R4 and R5 are hydrogen, amino, alkoxyalkyl, aminoalkyl, alkylaminoalkyl, dialkylaminoalkyl, or alkenyl, or phenyl, phenylalkyl or phenylalkenyl, heterocycyl, heterocyclylalkyl or heterocyclylalkenyl, each optionally substituted, provided that when R1 is optionally substituted phenyl at least one of R1, R4 and R5 is, or contains, a phenyl ring bearing at least one substituent selected from cyano, cyanoalkyl, nitro, aminocarbonylalkyl, halogenoalkoxy and radicals of the formulae -CONR6R7, -NHCOR8 or OR9 as defined herein, and the acid addition salts of compounds which contain a basic substituent; together with processes for their manufacture, pharmaceutical, veterinary and plant antifungal compositions, a method of treating fungal diseases in plants, and the use of the compounds for the manufacture of pharmaceutical or veterinary antifungal compositions.

  式中的 1，3-二氮唑-2-丙醇衍生物：- 1，3-二氮唑-2-丙醇衍生物 其中X和Y是N或CH，R'是任选取代的苯基、杂环基、杂环烷基、-烯基或-炔基，R2和R3是氢或烷基，R4和R5是氢、氨基、烷氧基烷基、氨基烷基、烷基氨基烷基、二烷基氨基烷基、或烯基、或苯基、苯基烷基或苯基烯基、杂环基、杂环烷基或杂环烷基，各自任选取代、条件是当 R1 是任选取代的苯基时，R1、R4 和 R5 中至少有一个是或含有一个苯基环，该苯基环上至少有一个取代基，该取代基可选自氰基、氰基烷基、硝基、氨基羰基烷基、卤代烷氧基和本文定义的-CONR6R7、-NHCOR8 或 OR9 式中的基团，以及含有碱性取代基的化合物的酸加成盐；连同其生产工艺、药用、兽用和植物抗真菌组合物、治疗植物真菌疾病的方法，以及使用这些化合物生产药用或兽用抗真菌组合物。
• Diphenylethane derivatives
  申请人：IMPERIAL CHEMICAL INDUSTRIES PLC

  公开号：EP0354689A1

  公开（公告）日：1990-02-14

  Diphenylethane derivatives of the formula are described; wherein R¹ is a heterocyclyl radical selected from the group consisting of 1,2,4-triazolyl, optionally-substituted imidazolyl, pyridyl and pyrimidinyl radicals; R² and R³, which may be the same or different, are each a hydrogen atom or a 1-6C alkyl radical; R⁴ and R⁵, which may be the same or different, are each a hydrogen or fluorine atom or a 1-6C alkyl radical; and A is a phenyl radical, optionally bearing one or more substituents selected from halogen atoms, cyano radicals or 1-4C halogenoalkyl or halogenoalkoxy radicals, Processes for their preparation are described, as is their use as aromatase inhibitors, for example in the treatment of cancer or as plant antifungal compounds.

  描述了式 所述的二苯基乙烷衍生物； 其中 R¹ 是杂环基，选自由 1，2，4-三唑基、任选取代的咪唑基、吡啶基和嘧啶基组成的组；R² 和 R³ 可以相同或不同，各自是氢原子或 1-6C 烷基；R⁴ 和 R⁵ 可以相同或不同，各自是氢原子或氟原子或 1-6C 烷基；A 是苯基，任选带有一个或多个选自卤素原子、氰基或 1-4C 卤代烷基或卤代烷氧基的取代基。