1-(1H-imidazol-1-yl)-4-phenyl-2-butanone | 741628-94-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(1H-imidazol-1-yl)-4-phenyl-2-butanone
• 英文别名: 1-(imidazol-1-yl)-4-phenylbutan-2-one；1-[4-phenylbutan-2-on-1-yl]imidazole；1-Azolyl-4-phenyl-2-butanone, 6a；1-imidazol-1-yl-4-phenylbutan-2-one
• CAS: 741628-94-4
• 化学式: C₁₃H₁₄N₂O
• 分子量: 214.267
• InChiKey: IIHVAAZDEQVTTO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  34.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(1H-imidazol-1-yl)-4-phenyl-2-butanone 在 盐酸 作用下， 以 水 、 异丙醇 为溶剂， 以86%的产率得到1-(1H-imidazol-1-yl)-4-phenyl-2-butanone hydrochloride
  参考文献：
  名称：

  WO2008/151437

  摘要：

  公开号：
• 作为产物：
  描述：

  苄基丙酮 在 溴 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 1-(1H-imidazol-1-yl)-4-phenyl-2-butanone
  参考文献：
  名称：

  Heme oxygenase inhibition by 2-oxy-substituted 1-(1H-imidazol-1-yl)-4-phenylbutanes: Effect of halogen substitution in the phenyl ring

  摘要：

  A series of 2-oxy-substituted 1-(1H-imidazol-1-yl)-4-phenylbutanes comprising imidazole-ketones, imidazole-dioxolanes, and imidazole-alcohols substituted with halogens in the phenyl ring were synthesized and evaluated as novel inhibitors of heme oxygenase which are structurally distinct from metalloporphyrins. The entire library of compounds was found to be highly active, with the bromine- and iodine-substituted derivatives being the most potent. The imidazole dioxolanes were all selective for the HO-1 isozyme (inducible) and exhibited substantially lower activity toward the HO-2 isozyme (constitutive). The corresponding imidazole-ketones and imidazole-alcohols showed selectivity toward HO-1 to a lesser degree than the similarly substituted imidazole-dioxotanes. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.02.034

文献信息

• Heme Oxygenase Inhibition by 2-Oxy-substituted 1-Azolyl-4-phenylbutanes: Effect of Variation of the Azole Moiety. X-Ray Crystal Structure of Human Heme Oxygenase-1 in Complex with 4-Phenyl-1-(1<i>H</i>-1,2,4-triazol-1-yl)-2-butanone
  作者：Gheorghe Roman、Mona N. Rahman、Dragic Vukomanovic、Zongchao Jia、Kanji Nakatsu、Walter A. Szarek

  DOI：10.1111/j.1747-0285.2009.00909.x

  日期：2010.1

  5‐substituted triazoles, identically 3,5‐disubstituted triazoles, 5‐substituted‐1H‐ and 5‐substituted‐2H‐tetrazoles proved to be detrimental to the inhibition of HO, with a few exceptions. The azole‐dioxolanes and the azole‐alcohols derived from the active azole‐ketones were synthesized also, but these inhibitors were less active than the corresponding imidazole‐based analogs. The first reported X‐ray crystal

  为抑制血红素加氧酶（血红素加氧酶-1和血红素加氧酶-2），设计并合成了一系列的1-偶氮基-4-苯基-2-丁酮。用其他唑类取代咪唑导致发现了新型的1 H -1,2,4-三唑和1 H-四唑类抑制剂，与咪唑类铅抑制剂等效。具有2 H-四唑或1 H的抑制剂‐1,2,3-三唑作为药效基团的效力较低。通过各种吸电子或给电子的，小的或庞大的基团，在咪唑的2或4（5）位置被单取代，或在咪唑的4和5位置相同的解离，以及用阵列代替传统的咪唑药效基团3或5取代的三唑，3,5-二取代的三唑，5取代的1 H和5取代的2 H除少数例外，四唑类被证明对HO的抑制是有害的。还合成了由活性唑酮衍生的唑二氧杂戊环酮和唑醇，但这些抑制剂的活性低于相应的基于咪唑的类似物。首次报道了人类血红素加氧酶-1与1,2,4-三唑基抑制剂（即4-苯基-1-（1 H -1,2,4-三唑-1）的复合物的X射线晶体结构yl）-2-丁酮也已确定。该抑制剂通过三唑部分中的N
• Thioketal substituted N-alkyl imidazoles
  申请人：Syntex (U.S.A.) Inc.

  公开号：US04359475A1

  公开（公告）日：1982-11-16

  Compounds of the formula: ##STR1## wherein R.sub.1 is phenyl optionally substituted with one or more substituents independently selected from the group consisting of lower alkyl, lower alkoxy, halo, or trifluoromethyl; Z is ethylene or propylene, optionally substituted with a single substituent which is lower alkyl; A is the integer 0, 1, 2, or 3; B is the integer 1, 2, or 3; and wherein the sum of A and B is 1, 2, 3 or 4; and the pharmaceutically acceptable acid addition salts thereof, said compounds being useful as spermicidal, antimicrobial and anticonvulsant agents.

  该公式化合物为：##STR1##其中R.sub.1是苯基，可选地被一个或多个取代基独立地选自以下组：低烷基，低烷氧基，卤素或三氟甲基；Z是乙烯或丙烯，可选地被一个低烷基取代；A是整数0、1、2或3；B是整数1、2或3；其中A和B的和为1、2、3或4；以及其药学上可接受的酸加盐，该化合物可用作杀精、抗微生物和抗癫痫药物。
• Compounds and Methods for Treating Cancer and Diseases of the Central Nervous System
  申请人：Gupta Ajay

  公开号：US20110319459A1

  公开（公告）日：2011-12-29

  Disclosed are compounds of the general formula (I): TC n D  (I), compositions comprising an effective amount of said compounds either alone or in combination with other chemotherapeutic agents, and methods useful for treating or preventing cancer and for inhibiting tumour tissue growth. These compounds attenuate the oxidative damage associated with increased heme-oxygenase activity and can reduce cell proliferation in transformed cells. In addition, the described compounds and compositions are useful as neuroprotectants and for treating or preventing neurodegenerative disorders and other diseases of the central nervous system.

  本发明涉及一般式（I）的化合物：TCnD（I），包括单独使用或与其他化疗药物联合使用的有效量的该化合物的组合物，以及用于治疗或预防癌症和抑制肿瘤组织生长的有用方法。这些化合物减弱了与增加血红素氧合酶活性相关的氧化损伤，并可以减少转化细胞中的细胞增殖。此外，所述化合物和组合物可用作神经保护剂，并用于治疗或预防中枢神经系统的神经退行性疾病和其他疾病。
• Derivatives of substituted N-alkylimidazoles, their preparation and pharmaceutical compositions containing them
  申请人：SYNTEX (U.S.A.) INC.

  公开号：EP0049565A2

  公开（公告）日：1982-04-14

  Compounds useful as anticonvulsant agents, antifungals and antibacterials are represented by the formula wherein R1 is phenyl optionally substituted by one or more substituents selected from the group consisting of halo, lower alkyl of one to four carbon atoms, lower alkoxy of one to four carbon atoms and trifluoromethyl; Z is ethylene or propylene optionally substituted by one or more lower alkyl groups of one to four carbon atoms; m is 1, 2, 3 or 4 and n is 0, 1, 2, or 3 with the proviso that the sum of m and n is 2, 3 or 4; and the pharmaceutically acceptable acid addition salts thereof. The ketone intermediates useful in preparing compounds of formula (I) also have anticonvulsant activity.

  可用作抗惊厥剂、抗真菌剂和抗菌剂的化合物由以下式子表示 其中 R1 是苯基，可任选被一个或多个取代基取代，这些取代基可从卤代、一至四个碳原子的低级烷基、一至四个碳原子的低级烷氧基和三氟甲基组成的组中选出；Z 是乙烯或丙烯，可任选被一个或多个一至四个碳原子的低级烷基取代；m 是 1、2、3 或 4，n 是 0、1、2 或 3，但 m 和 n 之和必须是 2、3 或 4；及其药学上可接受的酸加成盐。 用于制备式（I）化合物的酮中间体也具有抗惊厥活性。
• Spermicidal 1-bis(arylalkyl)alkylimidazoles
  申请人：SYNTEX (U.S.A.) INC.

  公开号：EP0064244A1

  公开（公告）日：1982-11-10

  New compounds of the formula wherein: Ar1 and Ar2 are each independently optionally substituted phenyl; R', R2 and R3 are each independently hydrogen or alkyl; a is an integer from 1-3; b is an integer from 1-3; c is an integer from 0-2; and d is an integer from 0-2, such that (c + d) equals 0-2; and the pharmaceutically acceptable non-toxic acid addition salts thereof, are spermicidal and, therefore, are useful as contraceptives.

  式中的新化合物 其中 Ar1 和 Ar2 各自独立地为任选取代的苯基； R'、R2 和 R3 各自独立地为氢或烷基 a 是 1-3 的整数 b 是 1-3 的整数 c 是 0-2 的整数；以及 d 是 0-2 的整数，这样 (c + d) 等于 0-2；其药学上可接受的无毒酸加成盐具有杀精子作用，因此可用作避孕药。