1-(5-甲基-2-苯基-1H-咪唑-4-基)乙酮 | 28824-91-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 1-(5-甲基-2-苯基-1H-咪唑-4-基)乙酮
• 英文名称: 4-Acetyl-5-methyl-2-phenyl-imidazol
• 英文别名: methyl 5-methyl-2-phenyl-4-imidazolyl ketone；1-(5-methyl-2-phenyl-1H-imidazol-4-yl)ethanone
• CAS: 28824-91-1
• 化学式: C₁₂H₁₂N₂O
• mdl: MFCD01098518
• 分子量: 200.24
• InChiKey: RAFHDKLDMHYNOT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.166
• 拓扑面积：
  45.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(5-甲基-2-苯基-1H-咪唑-4-基)乙酮 在 盐酸 、 三乙胺 作用下， 以 乙醇 、 水 为溶剂， 反应 8.0h， 生成 4-methyl-2-{[1-(5-methyl-2-phenyl-1H-imidazol-4-yl)ethylidene]hydrazono}-5-(2-phenylhydrazono)-2,5-dihydrothiazole
  参考文献：
  名称：

  Synthesis, antimicrobial, antioxidant, anti-hemolytic and cytotoxic evaluation of new imidazole-based heterocycles

  摘要：

  In the present work, 1-(5-methyl-2-phenyl-1H-imidazol-4-yl)ethanone 1 was prepared and used as a precursor for the synthesis of new thiazole, arylidiene and coumarin derivatives. The antimicrobial, antioxidant, anti-hemolytic, and cytotoxic activities of new compounds have been screened. Compound 12 showed an excellent antibacterial activity for all the tested bacteria with minimal inhibitory concentration (MIC) ranged between 21.9 and 43.8 mu g/mL While, compounds 2, 8 and 10a were the best antioxidant reagents using the DPPH method. Compounds 6a and 10b proved to exhibit potent anti-oxidative activity as reflected in the ability to inhibit lipid per-oxidation in rat brain and kidney homogenates and rate erythrocyte hemolysis. Compounds 6a proved to have the highest cytotoxic activity (81.9%) followed by 2, 6c, 7b and 12 using in vitro Ehrlich ascites assay. The details synthetic methods, spectroscopic data and biological results are recorded. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.01.062
• 作为产物：
  描述：

  2,3,4-戊三酮肟 (6ci,7ci,8ci,9ci) 以 二甲基亚砜 为溶剂， 反应 3.0h， 生成 1-(5-甲基-2-苯基-1H-咪唑-4-基)乙酮
  参考文献：
  名称：

  Veronese, A.C.; Cavicchioni, G.; Servadio, G., Journal of Heterocyclic Chemistry, 1980, vol. 17, p. 1723 - 1725

  摘要：

  DOI：

文献信息

• Substituted imidazolyl-alkyl-piperazine and -diazepine derivatives
  申请人：Syntex Pharmaceuticals, Ltd.

  公开号：US05043447A1

  公开（公告）日：1991-08-27

  Substituted imidazolyl-alkyl-piperazine and diazepine derivatives of Formula A: ##STR1## wherein: R.sup.1 is aryl, lower alkyl, cycloalkyl or hydrogen; R.sup.2 is aryl, lower alkyl or hydrogen; R.sup.3 is lower alkyl, hydroxy, or hydrogen; R.sup.4 is aryl or hydrogen; R.sup.5 is aryl or hydrogen; m is two or three; n is zero, one or two, provided that when R.sup.3 is hydroxy, n is one or two; and q is zero, one, two, or three; and the pharmaceutically acceptable salts thereof, are useful for treating mammals having any of a variety of disease states including: diseases treated by direct neuronal protection, such as ischemia including focal and global ischemia, spinal injuries, head trauma, and neurological diseases such as Alzheimer's and Huntington's chorea; diseases treated by inhibition of sodium ion, such as uremic and hyponatremic encephalopathy; and diseases treated with calcium channel antagonists, including: diseases treated by inhibiting cerebrovascular vasospasm and by cerebrovascular vasodilation, such as migraine, stroke, vasospasm due to subarachnoid hemorrhage, epilepsy or epileptic psychotic symptoms, and cerebrovascular ischemia induced by cocaine abuse; and cardiovascular diseases, such as hypertension, angina, stable and unstable angina, Prinzmetal angina, arrhythmia, thrombosis, embolism, and congestive heart failure such as chronic or acute cardiac failure; and ischemia of lower legs due to peripheral vascular disease, e.g., intermittent claudication; spasms of smooth muscle: such as the ureter, the bladder, uterine cramps, diuresis, and irritable bowel syndrome; and uses during surgery: such as bypass grafts, angiography, angioplasty, organ preservation during transplant, hypertensive crisis, or post operative hypertension.

  Formula A的咪唑基-烷基-哌嗪和二氮杂环衍生物：##STR1##其中：R.sup.1为芳基，较低烷基，环烷基或氢；R.sup.2为芳基，较低烷基或氢；R.sup.3为较低烷基，羟基或氢；R.sup.4为芳基或氢；R.sup.5为芳基或氢；m为二或三；n为零，一或二，但当R.sup.3为羟基时，n为一或二；q为零，一，二或三；及其药学上可接受的盐，用于治疗患有各种疾病状态的哺乳动物，包括：通过直接神经保护治疗的疾病，如缺血，包括局部和全局缺血，脊髓损伤，头部创伤以及阿尔茨海默病和亨廷顿舞蹈症等神经系统疾病；通过抑制钠离子治疗的疾病，如尿毒症和低钠性脑病；以及通过钙通道拮抗剂治疗的疾病，包括：通过抑制脑血管痉挛和脑血管扩张治疗的疾病，如偏头痛，中风，由蛛网膜下腔出血引起的血管痉挛，癫痫或癫痫性精神症状，以及可卡因滥用引起的脑血管缺血；以及心血管疾病，如高血压，心绞痛，稳定和不稳定性心绞痛，普林兹梅塔心绞痛，心律失常，血栓形成，栓塞，以及慢性或急性心力衰竭，以及由于外周血管疾病引起的下肢缺血，例如间歇性跛行；平滑肌痉挛：如输尿管，膀胱，子宫痉挛，利尿和肠易激综合征；以及手术期间的用途：如旁路移植，血管造影，血管成形术，器官移植期间的器官保护，高血压危机或术后高血压。
• 2-(substituted-1-piperazinyl)[1,2,4]triazolo[1,5-a]pyrimidines
  申请人：American Cyanamid Company

  公开号：US04582833A1

  公开（公告）日：1986-04-15

  This disclosure describes novel 2-(4-substituted-1-piperazinyl)[1,2,4]triazolo[1,5-a]pyrimidines useful as hypotensive agents.

  这项披露描述了作为降压药物有用的新型2-(4-取代-1-哌嗪基)[1,2,4]三唑[1,5-a]嘧啶。
• Method for the control of undesired plant species using
  申请人：American Cyanamid Company

  公开号：US04168964A1

  公开（公告）日：1979-09-25

  This disclosure describes herbicidal methods for the pre- and postemergence control of undesired mono- and dicotyledonous plants using substituted imidazo[1,5-d]-as-triazin-4(3H)-ones and substituted imidazo[1,5-d]-as-triazine-4(3H)-thiones.

  本公开描述了使用取代的咪唑[1,5-d]-嘧啶-4(3H)-酮和取代的咪唑[1,5-d]-嘧啶-4(3H)-硫醚来进行对不受欢迎的单子叶和双子叶植物的前期和后期除草的除草方法。
• Hypervalent Iodine in Synthesis 81: A One-Pot Procedure for the Synthesis of 1H-Imidazole Derivatives by Cyclocondensation of Ketones with [Hydroxy(tosyloxy)iodo]benzene and Amidines
  作者：Peng-Fei Zhang、Zhen-Chu Chen

  DOI：10.1055/s-2001-18059

  日期：——

  by cyclocondensation of ketones with [hydroxy(tosyloxy)iodo]benzene and selenoamides.6 Herein, we would like to report a one-pot procedure for the synthesis of imidazoles, which includes α-tosyloxylation of ketones with [hydroxy(tosyloxy)iodo]benzene in acetonitrile, followed by treatment with amidines in chloroform. The overall yields of imidazoles are 42–67% without isolation of any intermediates

  咪唑核存在于多种天然产物中，如维生素B12及其衍生物、1组氨酸衍生物、2咪唑核苷和核苷酸3。因此，咪唑核的合成变得越来越重要，文献报道了几种咪唑衍生物的合成。 4 作为我们针对在有机合成中使用高价碘试剂的计划的一部分，5 我们最近报道了通过酮与 [羟基（甲苯磺酰氧基）碘] 苯和硒酰胺的环缩合来方便合成硒唑。6 在此，我们希望报告合成咪唑的一锅法，包括在乙腈中用[羟基(甲苯磺酰氧基)碘]苯对酮进行α-甲苯磺酰氧基化，然后在氯仿中用脒处理。咪唑的总产率为 42-67%，无需分离任何中间体（方案 1）。
• Sustituted imidazolyl-alkyl-piperazine and -diazepine derivatives for
  申请人：Syntex Pharmaceuticals Ltd.

  公开号：US04935417A1

  公开（公告）日：1990-06-19

  Substituted imidazolyl-alkyl-piperazine and diazepine derivatives of Formula A: ##STR1## wherein: R.sup.1 is aryl, lower alkyl, cycloalkyl or hydrogen; R.sup.2 is aryl, lower alkyl or hydrogen; R.sup.3 lower alkyl, hydroxy, or hydrogen; R.sup.4 aryl or hydrogen; R.sup.5 aryl or hydrogen; m is two or three; n is zero, one or two, provided that when R.sup.3 hydroxy, n is one or two; and q is zero, one, two, or three; and the pharmaceutically acceptable salts thereof, are calcium channel antagonists useful for treating mammals having a variety of disease states, such as stroke, epilipsy, hypertension, angina, migraine, arrhythmia, thrombosis, embolism and also for treatment of spinal injuries.

  公式A的替代咪唑基-烷基哌嗪和二氮杂环衍生物： ##STR1## 其中：R.sup.1是芳基，低碳基，环烷基或氢；R.sup.2是芳基，低碳基或氢；R.sup.3是低碳基，羟基或氢；R.sup.4是芳基或氢；R.sup.5是芳基或氢；m为二或三；n为零，一或二，但当R.sup.3为羟基时，n为一或二；q为零，一，二或三；以及其药学上可接受的盐，用于治疗患有各种疾病状态的哺乳动物，如中风、癫痫、高血压、心绞痛、偏头痛、心律失常、血栓形成、栓塞以及脊髓损伤的治疗。