N-(5-甲基-1,2-恶唑-3-基)-1-(4-硝基苯基)甲亚胺 | 112633-39-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N-(5-甲基-1,2-恶唑-3-基)-1-(4-硝基苯基)甲亚胺
• 英文名称: (E)-N-(5-Methyl-1,2-oxazol-3-yl)-1-(4-nitrophenyl)methanimine
• 英文别名: N-(5-methyl-1,2-oxazol-3-yl)-1-(4-nitrophenyl)methanimine
• CAS: 112633-39-3
• 化学式: C₁₁H₉N₃O₃
• 分子量: 231.211
• InChiKey: FSNLLGSNBWLZNZ-UHFFFAOYSA-N

物化性质

• 熔点：
  117-119 °C
• 沸点：
  441.0±40.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 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：
  84.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(5-甲基-1,2-恶唑-3-基)-1-(4-硝基苯基)甲亚胺 在 三乙酰氧基硼氢化钠 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 3.5h， 以1.62 g的产率得到N-(4'-nitro)benzyl-N-(5-methyl-3-isoxazolyl)amine
  参考文献：
  名称：

  Isoxazole derivatives as potent transient receptor potential melastatin type 8 (TRPM8) agonists

  摘要：

  Modulation of the transient receptor potential melastatin type-8 (TRPM8), the receptor for menthol acting as the major sensor for peripheral innocuous cool temperatures, has several important applications in pharmaceutical, food and cosmetic industries. In the present study, we designed 12 isoxazole derivatives and tested their pharmacological properties both in F11 sensory neurons in vitro, and in an in vivo model of cold allodynia. In F11 sensory neurons, single-cell ca(2+)-imaging experiments revealed that, when compared to menthol, some newly-synthesized compounds were up to 200-fold more potent, though none of them showed an increased efficacy. Some isoxazole derivatives potentiated allodynic responses elicited by acetone when administered to rats subjected to sciatic nerve ligation; when compared to menthol, these compounds were efficacious at earlier (0-2 min) but not later (7-9 or 14-16 min) time points. Docking experiments performed in a human TRPM8 receptor model revealed that newly-synthesized compounds might adopt two possible conformations, thereby allowing to distinguish "menthol-like" compounds (characterized by high efficacy/low potency), and "icillin-like" compounds (with high potency/low efficacy). Collectively, these data provide rationale structure-activity relationships for isoxazole derivatives acting as TRPM8 agonists, and suggest their potential usefulness for cold-evoked analgesia. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.08.056
• 作为产物：
  描述：

  3-氨基-5-甲基异恶唑 、 对硝基苯甲醛 以 甲醇 为溶剂， 反应 0.5h， 生成 N-(5-甲基-1,2-恶唑-3-基)-1-(4-硝基苯基)甲亚胺
  参考文献：
  名称：

  氨基异恶唑和芳香醛反应的异常产物

  摘要：

  摘要 伯胺与醛反应通常会产生席夫碱。在这项工作中，我们介绍了在 5-甲基-3-氨基异恶唑 (3AMI) 或 3-甲基-5-反应中获得的产物的研究结果（NMR、ATR-FTIR、UV-Vis 和 X 射线）氨基异恶唑 (5AMI) 与 17 种不同的醛。基于结果，我们证明了这种简单而众所周知的反应并不总是导致获得典型的产品。此外，我们还讨论了所研究的邻羟基亚胺化合物在溶液和固态中优选的互变异构形式。了解赋予席夫碱的互变异构形式存在于溶液中和固态中，对于医学和药学以及配位化学的发展非常重要。

  DOI：

  10.1016/j.molstruc.2021.131320

文献信息

• New tricks of well-known aminoazoles in isocyanide-based multicomponent reactions and antibacterial activity of the compounds synthesized
  作者：Maryna V Murlykina、Maryna N Kornet、Sergey M Desenko、Svetlana V Shishkina、Oleg V Shishkin、Aleksander A Brazhko、Vladimir I Musatov、Erik V Van der Eycken、Valentin A Chebanov

  DOI：10.3762/bjoc.13.104

  日期：——

  novel features of a Groebke-Blackburn-Bienaymé cyclocondensation are established and discussed. The heterocycles obtained were evaluated for their antibacterial activity and several of them demonstrated a weak antimicrobial effect, but for most of the compounds a 30-50% increase in biomass of Gram-positive strains (mainly B. subtilis) compared to control was observed.

  在 Ugi 和 Groebke-Blackburn-Bienaymé 多组分反应中，对著名的氨基唑、3-氨基-5-甲基异恶唑和 5-氨基-N-芳基-1H-吡唑-4-甲酰胺作为胺组分进行了研究。发现了氨基唑在 Ugi 四组分反应中应用的第一个例子，并建立并讨论了 Groebke-Blackburn-Bienaymé 环缩合的新特征。对获得的杂环化合物的抗菌活性进行了评估，其中一些化合物显示出较弱的抗菌作用，但对于大多数化合物而言，观察到与对照相比，革兰氏阳性菌株（主要是枯草芽孢杆菌）的生物量增加了 30-50%。
• Squaramide-catalysed enantionselective Mannich reaction of imines bearing a heterocycle with malonates
  作者：Hai-Xiao He、Da-Ming Du

  DOI：10.1039/c3ra43260b

  日期：——

  An efficient enantioselective Mannich reaction of imines bearing a heterocycle with malonates catalysed by a cinchona-based squaramide organocatalyst has been developed. This catalytic asymmetric reaction afforded the β-amino ester derivatives containing a heterocycle moiety in high yields (up to 99%) and excellent enantioselectivities (up to 98%) in most cases. The imines with an electron-withdrawing

  已经开发了一种有效的对映选择性曼尼奇反应，该亚胺带有一个由金鸡纳基方酸酰胺有机催化剂催化的丙二酸酯。该催化不对称反应在大多数情况下以高产率（高达99％）和优异的对映选择性（高达98％）提供了含有杂环部分的β-氨基酯衍生物。在该反应中，具有吸电子基团的亚胺比带有电子给体基团的亚胺具有更好的收率。
• Synthesis and antidiabetic performance of β-amino ketone containing nabumetone moiety
  作者：Hang Wang、Ju-fang Yan、Xiao-li Song、Li Fan、Jin Xu、Guang-ming Zhou、Li Jiang、Da-cheng Yang

  DOI：10.1016/j.bmc.2012.01.028

  日期：2012.3

  We wish to report the further design and improved synthesis that resulted in two series of target molecules, TM-1 and TM-2, with remarkably simplified structures containing beta-amino ketone of discrete nabumetone moiety. These were obtained via a 'one-pot, two-step, three-component' protocol of Mannich reaction with yield up to 97%. A total of 28 out of 31 new compounds were characterized using H-1 NMR, C-13 NMR, ESI MS and HRMS techniques. Studies on their antidiabetic activities, screened in vitro at 10 mu g mL (1) level, indicate that TM-2 possesses peroxisome proliferator-activated receptor activation and alpha-glucosidase inhibition activity significantly stronger than that of TM-1, and also that of the series B compounds that were previously synthesized by the group. Analysis of the structure-activity relationship points to the sulfanilamide unit as the most probable potent group of b-amino ketone and, on the basis of which, a tangible strategy is presented for the development of new antidiabetic drugs. (C) 2012 Elsevier Ltd. All rights reserved.
• Rajanarendar; Raju; Reddy, M. Nagi, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2011, vol. 50, # 2, p. 223 - 228
  作者：Rajanarendar、Raju、Reddy, M. Nagi、Reddy, K. Govardhan

  DOI：——

  日期：——
• Rajanarendar; Afzal; Ramu, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2003, vol. 42, # 4, p. 927 - 930
  作者：Rajanarendar、Afzal、Ramu

  DOI：——

  日期：——