(Z)-2,3-dihydro-3-(1H-imidazol-1-yl)-4H-1-benzopyran-4-one oxime | 485386-04-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (Z)-2,3-dihydro-3-(1H-imidazol-1-yl)-4H-1-benzopyran-4-one oxime
• 英文别名: (NZ)-N-(3-imidazol-1-yl-2,3-dihydrochromen-4-ylidene)hydroxylamine
• CAS: 485386-04-7
• 化学式: C₁₂H₁₁N₃O₂
• 分子量: 229.238
• InChiKey: XNIOEJPXDHWIHV-OWBHPGMISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  59.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,4-二氯氯苄 、 (Z)-2,3-dihydro-3-(1H-imidazol-1-yl)-4H-1-benzopyran-4-one oxime 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 N-[(3,4-dichlorophenyl)methoxy]-3-imidazol-1-yl-chroman-4-imine
  参考文献：
  名称：

  Stereoselective Synthesis and in Vitro Antifungal Evaluation of (E)- and (Z)-Imidazolylchromanone Oxime Ethers

  摘要：

  A series of (E)- and (Z)-2,3-dihydro-3-(1 H-imidazol-1 -yl)-4H-1 -benzopyran-4-one oxime ethers have been synthesized and tested for antifungal activity Most compounds showed moderate to potent in vitro antifungal activity. Among the tested compounds, compound (E)-3 d was the most active agent against Candida albicans and Aspergillus niger, and compounds (Z)-(3 a) and (E)-3 a were the most potent compounds against Microsporum gypseum. Detailed stereoselective synthesis, spectroscopic, and biological data are reported.

  DOI：

  10.1002/1521-4184(200209)335:7<318::aid-ardp318>3.0.co;2-o
• 作为产物：
  描述：

  2-(1H-imidazol-1-yl)-2'-hydroxyacetophenone 在 盐酸羟胺 作用下， 以 甲醇 、 溶剂黄146 为溶剂， 生成 (Z)-2,3-dihydro-3-(1H-imidazol-1-yl)-4H-1-benzopyran-4-one oxime
  参考文献：
  名称：

  Stereoselective Synthesis and in Vitro Antifungal Evaluation of (E)- and (Z)-Imidazolylchromanone Oxime Ethers

  摘要：

  A series of (E)- and (Z)-2,3-dihydro-3-(1 H-imidazol-1 -yl)-4H-1 -benzopyran-4-one oxime ethers have been synthesized and tested for antifungal activity Most compounds showed moderate to potent in vitro antifungal activity. Among the tested compounds, compound (E)-3 d was the most active agent against Candida albicans and Aspergillus niger, and compounds (Z)-(3 a) and (E)-3 a were the most potent compounds against Microsporum gypseum. Detailed stereoselective synthesis, spectroscopic, and biological data are reported.

  DOI：

  10.1002/1521-4184(200209)335:7<318::aid-ardp318>3.0.co;2-o

文献信息

• N-imidazolyl derivatives of substituted alkoxyimino tetrahydronaphthalenes and chromans
  申请人：PHARMACIA S.p.A.

  公开号：EP0499444A1

  公开（公告）日：1992-08-19

  The invention provides new imidazole containing alkoxyimino derivatives of tetrahydronaphthalene and chroman of general formula (I) wherein    Z is -CH₂-or-O-;    m is an integer of 1 to 4;    n is zero or 1;    T is a straight or branched, saturated or unsaturatrd C₁-C₆ hydrocarbon chain, or a phenylene radical;    A is a bond or a divalent group consisting of-Si(R′R˝)-; -O-CH₂-,-CF₃-,C(R′R˝)-,vinylene or isopropenylene, wherein each of R′ and R˝being the same or different is hydrogen or C₁-C₄ alkyl;    R is hydrogen or C₁-C₄ alkyl;    R₁ and R₂, being the same, are hydrogen or methyl, or one of R₁ and R₂ is hydrogen and the other is a) a C₁-C₈ alkyl group; b) a C₅-C₈ cycloalkyl or C₅-C₈ cycloalkyl-C₁-C₄ alkyl group, wherein the cycloalkyl group or moiety is unsubstituted or substituted by 1 to 4 C₁-C₄ alkyl groups; or c) an aryl or aryl-C₁-C₄ alkyl group, wherein the aryl group or the aryl moiety is unsubstituted or substituted by 1 to 4 substituents independently chosen from halogen, hydroxy, C₁-C₄ alkyl, trihalo-C₁-C₄ alkyl, C₁-C₄ alkoxy, C₁-C₄ alkylthio and C₁-C₄ alkylsulfonyl;    R₃ is hydrogen or a substituent chosen from halogen, hydroxy, C₁-C₄ alkyl, trihalo-C₁-C₄ alkyl, C₁-C₄ alkoxy, C₁-C₄ alkylthio and C₁-C₄ alkylsulfonyl;    R₄ is an -OR₅, or -N(R₅ R₆)group, wherein each of R₅ and R₆ independently is hydrogen, C₁-C₆ alkyl, phenyl or benzyl;    and the pharmaceutically acceptable salts thereof, which are useful in the treatment of a disease state in which an anhancement of TxA₂ synthesis exerts a pathogenic effect.

  本发明提供了通式(I)为四氢萘和铬烷的含烷氧基亚氨基的新咪唑衍生物 其中 Z 是-CH₂-或-O-； m 是 1 至 4 的整数 n 为 0 或 1； T 是直链或支链、饱和或不饱和 C₁-C₆烃链，或亚苯基； A 是键或由下列组成的二价基团：-Si(R′R˝)-；-O-CH₂-、-CF₃-、C(R′R˝)-、乙烯基或异亚丙烯基，其中 R′和 R˝ 不论相同或不同均为氢或 C₁-C₄ 烷基； R 是氢或 C₁-C₄ 烷基； R₁和R₂若相同，则为氢或甲基，或R₁和R₂中的一个为氢，另一个为 a) C₁-C₈ 烷基； b) C₅-C₈ 环烷基或 C₅-C₈ 环烷基-C₁-C₄ 烷基，其中环烷基或分子未被取代或被 1 至 4 个 C₁-C₄ 烷基取代；或 c) 芳基或芳基-C₁-C₄烷基，其中芳基或芳基分子未被取代或被 1 至 4 个独立选自卤素的取代基取代、羟基、C₁-C₄ 烷基、三卤代-C₁-C₄ 烷基、C₁-C₄ 烷氧基、C₁-C₄ 烷硫基和 C₁-C₄ 烷磺酰基； R₃ 是氢或选自卤素、羟基、C₁-C₄ 烷基、三卤代-C₁-C₄ 烷基、C₁-C₄ 烷氧基、C₁-C₄ 烷硫基和 C₁-C₄ 烷磺酰基的取代基； R₄ 是 -OR₅，或 -N(R₅ R₆)基团，其中 R₅ 和 R₆ 各自独立地是氢、C₁-C₆ 烷基、苯基或苄基； 及其药学上可接受的盐类，可用于治疗 TxA₂合成增强产生致病作用的疾病。
• Imidazolylchromanone oxime ethers as potential anticonvulsant agents: Anticonvulsive evaluation in PTZ-kindling model of epilepsy and SAR study
  作者：Saeed Emami、Abbas Kebriaeezadeh、Nematollah Ahangar、Reza Khorasani

  DOI：10.1016/j.bmcl.2010.12.021

  日期：2011.1

  As a continuation of our efforts to develop the azolylchromanone derivatives as potential anticonvulsant agents, we explored (Z)- and (E)-oxime ether derivatives of imidazolylchromanones bearing different lipophilic O-benzyl groups and tested their anticonvulsant activities in PTZ-kindling model of epilepsy. O-(2,4-Dichlorobenzyl) oximes 8a, 16a and 20a were significantly effective in delaying the onset of the PTZ-evoked seizures at the dose of 30 mg/kg in kindled animals. The most effective compounds in delaying seizures were 7-chlorochromanone-O-(2,4-dichlorobenzyl) oximes 8a and 20a. SAR studies showed that introduction of a chlorine atom to the 7-position and/or a methyl group to the 2-position of the chroman ring resulted in an improvement of anti-seizure efficacy in O-(2,4-dichlorobenzyl) oxime series. (C) 2010 Elsevier Ltd. All rights reserved.
• US5246956A
  申请人：——

  公开号：US5246956A

  公开（公告）日：1993-09-21
• Stereoselective Synthesis and in Vitro Antifungal Evaluation of (E)- and (Z)-Imidazolylchromanone Oxime Ethers
  作者：Saeed Emami、Mehraban Falahati、Ali Banifatemi、Kayvan Moshiri、Abbas Shafiee

  DOI：10.1002/1521-4184(200209)335:7<318::aid-ardp318>3.0.co;2-o

  日期：2002.9

  A series of (E)- and (Z)-2,3-dihydro-3-(1 H-imidazol-1 -yl)-4H-1 -benzopyran-4-one oxime ethers have been synthesized and tested for antifungal activity Most compounds showed moderate to potent in vitro antifungal activity. Among the tested compounds, compound (E)-3 d was the most active agent against Candida albicans and Aspergillus niger, and compounds (Z)-(3 a) and (E)-3 a were the most potent compounds against Microsporum gypseum. Detailed stereoselective synthesis, spectroscopic, and biological data are reported.
• Azolylchromans as a novel scaffold for anticonvulsant activity
  作者：Saeed Emami、Abbas Kebriaeezadeh、Mohammad Jafar Zamani、Abbas Shafiee

  DOI：10.1016/j.bmcl.2006.01.004

  日期：2006.4

  A series of azolylchroman derivatives were prepared as conformationally constrained analogs of (arylalkyl)azole anticonvulsants. The anticonvulsant activities of the compounds were evaluated by determining seizure latency and protective effect against pentylenetetrazole (PTZ)-induced lethal convulsions in mice at a dose of 5 mg/kg. Among these compounds, 7-chloro-3-(1H-imidazol-1-yl)chroman-4-one and 3-(1H-1.2,4-triazol-1-yl)chroman-4-one exhibited significant action in delaying seizures as well as effective protection against PTZ-induced seizures and deaths. (C) 2006 Elsevier Ltd. All rights reserved.