1-methyl-2-phenyl-1H-imidazole-5-carboxaldehyde | 94938-03-1

• 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-methyl-2-phenyl-1H-imidazole-5-carboxaldehyde
• 英文别名: 1-methyl-2-phenyl-1H-imidazole-5-carbaldehyde；3-methyl-2-phenylimidazole-4-carbaldehyde
• CAS: 94938-03-1
• 化学式: C₁₁H₁₀N₂O
• mdl: MFCD08703273
• 分子量: 186.213
• InChiKey: MTBHIZCUPAVJLC-UHFFFAOYSA-N

物化性质

• 熔点：
  94-95 °C
• 沸点：
  377.6±34.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  34.9
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2933290090

反应信息

• 作为反应物：
  描述：

  N-叔丁基羟胺盐酸盐 、 1-methyl-2-phenyl-1H-imidazole-5-carboxaldehyde 在 碳酸氢钠 作用下， 以 乙醇 为溶剂， 反应 16.0h， 以62%的产率得到(Z)-α-[1-Methyl-2-phenyl-1H-imidazol-5-yl]-N-tert-butylnitrone
  参考文献：
  名称：

  Synthesis, Structure, and Neuroprotective Properties of Novel Imidazolyl Nitrones

  摘要：

  A new series of imidazolyl nitrones spin traps has been synthesized and evaluated pharmacologically. The salient structural feature of these molecules is the presence of an imidazole moiety substituted by aromatic or heteroaromatic cycles. This connectivity imparts to the nitrone superior neuroprotective properties in vivo and in parallel reduced side effects and toxicity. Thus compound 6a (a 2-phenylimidazolyl nitrone) administered intraperitoneally protects (80%) mice from lethality induced by an intracerebroventricular administration of tert-butyl hydroperoxide (t-BHP) an oxidant capable of inducing neurodegenerative processes. Administration of the archetypal nitrone phenyl-tert-butyl nitrone (PBN) at an equimolar dose also affords some protection (60%) in this test. However, this activity is accompanied by hypothermia, whereas no such effect is apparent for 6a. Moreover, previously prepared nonsubstituted or alkyl-substituted imidazolyl nitrones were shown to be extremely toxic to rats in contrast to the compounds prepared in this study. The observed activities in vivo correlate well with the calculated partition coefficients (ClogP) and HOMO energy level.

  DOI：

  10.1021/jm991154w
• 作为产物：
  描述：

  N-甲基马尿酸 在 manganese(IV) oxide 、 lithium aluminium tetrahydride 、 sodium hydride 、 potassium carbonate 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 1-methyl-2-phenyl-1H-imidazole-5-carboxaldehyde
  参考文献：
  名称：

  Convenient Synthesis of 5-Trifluoroacetylated Imidazoles by Ring Transformation of Mesoionic 1,3-Oxazolium-5-olates.

  摘要：

  中性离子型 4-三氟乙酰基-1, 3-噁唑鎓盐-5-醇盐（1），是通过N-氨酰-N-烷基甘氨酸（2）与三氟乙酸酐反应得到的，能够与胍类化合物反应，生成5-三氟乙酰基咪唑（3），产率适中。这一新颖的环转化反应是通过胍类对环的C-2位的初步攻击实现的。

  DOI：

  10.1248/cpb.48.410

文献信息

• [EN] 3-'4-HETEROCYCLYL -1,2,3,-TRIAZOL-1-YL!-N-ARYL-BENZAMIDES AS INHIBITORS OF THE CYTOKINES PRODUCTION FOR THE TREATMENT OF CHRONIC INFLAMMATORY DISEASES<br/>[FR] 3-'4-HETEROCYCLYL -1,2,3,-TRIAZOL-1-YL-N-ARYL-BENZAMIDES EN TANT QU'INHIBITEURS DE LA PRODUCTION DE CYTOKINES POUR LE TRAITEMENT DE MALADIES INFLAMMATOIRES
  申请人：BOEHRINGER INGELHEIM PHARMA

  公开号：WO2005090333A1

  公开（公告）日：2005-09-29

  Disclosed compounds of formula (I), which inhibit production of cytokines involved in inflammatory processes and are thus useful for treating diseases and pathological conditions involving inflammation such as chronic inflammatory disease. Also disclosed are processes for preparing these compounds and pharmaceutical compositions comprising these compounds.

  公开的化合物式(I)，可以抑制与炎症过程有关的细胞因子的产生，因此可用于治疗涉及炎症的疾病和病理状况，如慢性炎症性疾病。还公开了制备这些化合物的方法以及包含这些化合物的药物组合物。
• [EN] PIPERIDINE-CONTAINING COMPOUNDS AND USE THEREOF<br/>[FR] COMPOSÉS CONTENANT DE LA PIPÉRIDINE ET LEURS UTILISATIONS
  申请人：ARRAY BIOPHARMA INC

  公开号：WO2010080864A1

  公开（公告）日：2010-07-15

  A method for preventing and/or treating a metabolic disease, cerebrovascular disease, etc. which comprises administering to a mammal an effective amount of the compound of the formula (I) wherein all symbols have the same meanings as defined in the specification; a salt thereof, an N-oxide thereof, a solvate thereof, or a prodrug thereof. And a novel compound of the formula (I-1): wherein all symbols have the same meanings as defined in the specification; a salt thereof, an N-oxide thereof, a solvate thereof, or a prodrug thereof has an anti-diabetic effect and a neuroprotective effect. Accordingly, the compound of the formula (I) and the compound of the formula (I-1) are useful in a method for preventing and/or treating for a metabolic disease such as diabetes, cerebrovascular disease such as stroke, etc.

  一种预防和/或治疗代谢性疾病、脑血管疾病等的方法，包括向哺乳动物施用化合物的有效量，其化学式为(I)，其中所有符号的含义与规范中定义的相同；其盐、N-氧化物、溶剂合物或前药。以及化学式(I-1)的新化合物：其中所有符号的含义与规范中定义的相同；其盐、N-氧化物、溶剂合物或前药具有抗糖尿病作用和神经保护作用。因此，化合物(I)和化合物(I-1)在预防和/或治疗代谢性疾病如糖尿病、脑血管疾病如中风等方面是有用的。
• A novel ring transformation of mesoionic 1,3-oxazolium-5-olates into 5-trifluoroacetylated and 5-perfluoroacylated imidazoles by reaction with amidines
  作者：Masami Kawase

  DOI：10.1039/c39940002101

  日期：——

  Treatment of mesoionic 1,3-oxazolium-5-olates with amidines causes a novel ring transformation affording 5-trifluoroacetyl- and 5-perfluoroacyl-imidazoles in moderate yields.

  使用亚胺类化合物处理介离子1,3-噁唑鎓-5-醇盐可引发一种新型环转化反应，中等收率地合成5-三氟乙酰基和5-全氟酰基咪唑。
• Cardiotonic agents. 3. Synthesis and biological activity of novel 6-(substituted 1H-imidazol-4(5)-yl)-3(2H)-pyridazinones
  作者：Ila Sircar、George Bobowski、James A. Bristol、Ronald E. Weishaar、Dale B. Evans

  DOI：10.1021/jm00152a015

  日期：1986.2

  Several 6-(substituted 1H-imidazol-4(5)-yl)-3(2H)-pyridazinones were synthesized and evaluated for positive inotropic activity. The 1H-imidazol-4-yl regioisomers 4,5-dihydro-6-(1-methyl-2-phenyl-1H-imidazol-4-yl)-3(2H)-pyridazinone (25a) and 6-(1-methyl-2-phenyl-1H-imidazol-4-yl)-3(2H)-pyridazinone (28a) were potent positive inotropic agents. By contrast, the corresponding 1H-imidazol-5-yl regioisomers

  几个6-（取代的1H-咪唑-4（5）-基）-3（2H）-哒嗪酮被合成并评估其正性肌力活性。1H-咪唑-4-基区域异构体4,5-二氢-6-（1-甲基-2-苯基-1H-咪唑-4-基）-3（2H）-哒嗪酮（25a）和6-（1-甲基-2-苯基-1H-咪唑-4-基）-3（2H）-哒嗪酮（28a）是有效的正性肌力药。相比之下，相应的1H-咪唑-5-基区域异构体25b和​​28b只是弱的正性肌力药。化合物25a和28a也是心脏磷酸二酯酶部分III的有效抑制剂。
• Anti-cytokine heterocyclic compounds
  申请人：Cogan Derek

  公开号：US20060079519A1

  公开（公告）日：2006-04-13

  Disclosed compounds of formula (I) which inhibit production of cytokines involved in inflammatory processes and are thus useful for treating diseases and pathological conditions involving inflammation such as chronic inflammatory disease. Also disclosed are processes for preparing these compounds and pharmaceutical compositions comprising these compounds.

  公开的式子为（I）的化合物，其抑制涉及炎症过程的细胞因子的产生，并因此有用于治疗涉及炎症的疾病和病理情况，如慢性炎症性疾病。还公开了制备这些化合物的过程和包含这些化合物的制药组合物。