N-(2,6-二甲基苯基)-4-硝基-苯甲酰胺 | 64594-44-1

• 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-(2,6-二甲基苯基)-4-硝基-苯甲酰胺
• 英文名称: 4-Nitro-N-(2,6-dimethylphenyl)benzamide
• 英文别名: N-(2,6-dimethylphenyl)-4-nitrobenzamide；4-nitro-benzoic acid-(2,6-dimethyl-anilide)；4-Nitro-benzoesaeure-(2,6-dimethyl-anilid)；N-(2,6-dimethylphenyl)-4-nitro-benzamide
• CAS: 64594-44-1
• 化学式: C₁₅H₁₄N₂O₃
• mdl: MFCD00034008
• 分子量: 270.288
• InChiKey: WBLNADQPUSRQIV-UHFFFAOYSA-N

物化性质

• 熔点：
  193-196 °C
• 沸点：
  357.8±42.0 °C(Predicted)
• 密度：
  1.270±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  74.9
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2924299090

反应信息

• 作为反应物：
  描述：

  N-(2,6-二甲基苯基)-4-硝基-苯甲酰胺 在 palladium on activated charcoal 硫酸 、 环己烯 、 sodium nitrite 作用下， 以 异丙醇 为溶剂， 反应 8.5h， 生成 4-Hydroxy-N-(2,6-dimethylphenyl)benzamide
  参考文献：
  名称：

  Anticonvulsant Activity and Interactions with Neuronal Voltage-Dependent Sodium Channel of Analogues of Ameltolide

  摘要：

  Fifteen compounds related to ameltolide (LY 201116) were studied for (i) anticonvulsant potential in the maximal electroshock-induced seizures (MES) and the subcutaneous pentylenetetrazol (sc Ptz) tests in mice and rats and (ii) interactions with neuronal voltage-dependent sodium channels. Compounds were chosen ranging in anticonvulsant activity in mice from very active to inactive. The active compounds were defined as those protecting 50% of the animals at doses between 10 and 50 mu mol/kg and inactive compounds as those protecting 50% of the animals at doses greater than 1 mmol/kg. The series studied included three N-(2,6-dimethylphenyl)benzamides (compounds 1, 2 (ameltolide), and 3), three N-(2,2,6,6-tetramethyl)piperidinyl-4-benzamides (compounds 4, 5, 6), one phenylthiourea (compound 7), five N-(2,6-dimethylphenyl)phthalimides (compounds 8, 9, 10, 13, and 14), two N-phenylphthalimide derivatives (compounds 11 and 12), and one N-(2,2,6,6-tetramethyl)piperidinyl-4-phtalimide (compound 15). Phenytoin (PHT) was employed as the reference prototype antiepileptic drug. After inital screening in mice, compounds 1, 2, 3, 5, 8, 9, 10, 13, and 14 were selected for further testing in rats. Anticonvulsant ED(50)s (effective doses in at least 50% of animals tested) of compounds in the MES test were determined in rats dosed orally and amounted to 52 (1), 135 (2), 284 (3), 31 (8), 131 (9), 25 (10), 369 (13), 354 (14), and 121 (PHT) mu mol/kg, compound 5 presenting with an ED50 value higher than 650 mu mol/kg. In our hands, the apparent IC(50)s (inhibitory concentrations 50) of compounds toward binding to rat brain synaptosomes of [H-3]batrachotoxinin-A-20 alpha-benzoate were 0.25 (1), 0.97 (2), 0.35 (3), 25.8 (5), 161.3 (8), 183.5 (9), 0.11 (10), 1.86 (13), 47.8 (14), and 0.86 (PHT) mu M. The relationship between the activity in the MES test and the capacity to interact in vitro with neuronal voltage-dependent sodium channels and the fact that the IC50 values obtained in the in vitro test are close to the brain concentrations at which anticonvulsant activities are reported to occur for ameltolide strongly suggest that the anticonvulsant properties of most compounds tested could be a direct result of their interaction with the neuronal voltage-dependent sodium channel.

  DOI：

  10.1021/jm9608772
• 作为产物：
  描述：

  对硝基苯甲酸 在 氯化亚砜 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 29.0h， 生成 N-(2,6-二甲基苯基)-4-硝基-苯甲酰胺
  参考文献：
  名称：

  五元杂芳环稠合嘧啶衍生物：设计，合成和刺猬信号通路抑制研究。

  摘要：

  一系列新颖的五元杂芳环稠合嘧啶衍生物，包括嘌呤，吡咯并[2,3- d ]嘧啶，吡咯并[3,2- d ]嘧啶，噻吩并[2,3- d ]嘧啶，噻吩并[3， 2- d ]嘧啶和呋喃[3,2- d已经确定]嘧啶是刺猬蛋白信号传导途径的有效抑制剂。描述了这些化合物的合成和SAR。在这一新的刺猬信号通路抑制剂系列中，与vismodegib相比，大多数化合物均表现出显着的抑制活性，这表明五元杂芳环稠合嘧啶在当前报道的刺猬信号通路抑制剂的结构骨架中脱颖而出，成为令人鼓舞的支架，值得更多关注探索和进一步调查。

  DOI：

  10.1016/j.bmcl.2014.05.066

文献信息

• Synthesis and anticonvulsant activity of some 4-nitro-N-phenylbenzamides
  作者：V Bailleux、L Vallée、JP Nuyts、G Hamoir、JH Poupaert、JP Stables、J Vamecq

  DOI：10.1016/0223-5234(96)88254-7

  日期：1995.1

  A short series of 4-nitro-N-phenylbenzamides was synthesized and evaluated for anticonvulsant properties and neurotoxicity. In mice dosed intraperitoneally, three of the four 4-nitro-N-phenylbenzamides were efficient in the maximal electroshock-induced seizure (MES) test, especially N-(2,6-dimethylphenyl)-4-nitrobenzamide (ED(50) value in the MES test = 31.8 mumol/kg, TD(50) = 166.9 mumol/kg, protective

  合成了简短的4-硝基-N-苯基苯甲酰胺系列，并评估了其抗惊厥性质和神经毒性。在腹膜内给药的小鼠中，四种4-硝基-N-苯基苯甲酰胺中的三种在最大电击诱发癫痫发作（MES）测试中有效，尤其是N-（2,6-二甲基苯基）-4-硝基苯甲酰胺（ED（50）值在MES测试中= 31.8摩尔/千克，TD（50）= 166.9摩尔/千克，保护指数[PI] = 5.2）和N-（2-氯-6-甲基苯基）-4-硝基苯甲酰胺（ED（50）值在MES测试中= 90.3摩尔/千克，TD（50）= 1.068摩尔/千克，PI = 11.8）。还发现后者的4-硝基-N-苯基苯甲酰胺对皮下戊四烯（sc Ptz）引起的癫痫发作具有活性，并被选择用于口服给药的大鼠中作进一步评估。在这些条件下，在MES测试中发现N-（2-氯-6-甲基苯基）-4-硝基苯甲酰胺
• Intramolecular charge transfer with N-benzoylaminonaphthalenes. 1-Aminonaphthalene versus 2-aminonaphthalene as electron donors
  作者：Xuan Zhang、Chun-Hua Liu、Li-Hong Liu、Fang-Ying Wu、Lin Guo、Xiang-Ying Sun、Chao-Jie Wang、Yun-Bao Jiang

  DOI：10.1039/b210106h

  日期：2003.2.11

  derivatives in cyclohexane and was assigned to the CT state by the observation of a substantial red shift with increasing solvent polarity or with increasing electron-withdrawing ability of the substituent. The CT emission energies were found to follow a linear relationship with the Hammett constant of the substituent and the value of the linear slope for 1-NBAs (-0.45 eV) was higher than that of 2-NBAs (-0

  制备了在苯甲酰基苯环的对位或间位具有不同取代基的N-（取代-苯甲酰基）-1-氨基萘和N-（取代-苯甲酰基）-2-氨基萘（1-NBA和2-NBA）使用类苯甲酰苯胺电荷转移作为探针反应，探测1-氨基萘（1-AN）和2-氨基萘（2-AN）之间的差异。对于在环己烷中所有制备的氨基萘衍生物，发现了异常的长波发射，并且通过观察到随着溶剂极性的增加或取代基的吸电子能力的增加而发生的大幅度红移，将其分配为CT状态。发现CT发射能量与取代基的Hammett常数和1-NBA（-0。45 eV高于2-NBA（-0.35 eV），后者与苯胺衍生物（BAs，-0.345 eV）接近。这表明在1-NBA的CT状态下，电荷分离的程度更高，其中完全放电分离是通过CT发射能量的线性下降率为-1.00的降低电势依赖性建立的。通过观察发现，当对位，间位和对位时，苯甲酰基取代的BA的相应线性斜率保持不变，从而排除了1-NBA和2
• Anticonvulsant method and formulations
  申请人：Research Corporation

  公开号：US05064862A1

  公开（公告）日：1991-11-12

  This invention relates to certain aminobenzanilide compounds, and to the use, in the treatment of mammals, of certain aminobenzanilide compounds as anticonvulsant agents.

  本发明涉及某些氨基苯甲酰胺化合物，以及在治疗哺乳动物时使用某些氨基苯甲酰胺化合物作为抗惊厥药物。
• Bourhim, Mustapha; Poupaert, Jacques H.; Stables, James P., Arzneimittel-Forschung/Drug Research, 1999, vol. 49, # 2, p. 81 - 87
  作者：Bourhim, Mustapha、Poupaert, Jacques H.、Stables, James P.、Vallee, Louis、Vamecq, Joseph

  DOI：——

  日期：——
• Design, synthesis and structure–activity relationship of new HSL inhibitors guided by pharmacophore models
  作者：Jumana D. Al-Shawabkeh、Afaf H. Al-Nadaf、Lina A. Dahabiyeh、Mutasem O. Taha

  DOI：10.1007/s00044-013-0616-2

  日期：2014.1

  Hormone-sensitive lipase (HSL) is a critical enzyme involved in the hormonally regulated release of fatty acids and glycerol from adipocyte lipid stores. Its inhibition may improve insulin sensitivity and blood glucose handling in type 2 diabetes. Accordingly, many small-molecule HSL inhibitors have recently been identified. In continuation of our efforts for discovery of new HSL inhibitors, we prepared a variety of esters, amides, sulfonamides and sulfonate esters capable of fitting two pharmacophore models that we developed and published earlier. The tested compounds were synthesized via coupling reactions of aroyl chlorides or sulfonyl chlorides with phenols, amines and related derivatives. Our efforts led to the identification of interesting compounds of low micromolar anti-HSL bioactivities, which have potential to be developed into effective antidiabetic agents.

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