2'-甲基-5'-硝基苯甲酰苯胺 | 4771-07-7

• 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: 2'-甲基-5'-硝基苯甲酰苯胺
• 英文名称: N-(2-methyl-5-nitrophenyl)benzamide
• CAS: 4771-07-7
• 化学式: C₁₄H₁₂N₂O₃
• mdl: MFCD00430481
• 分子量: 256.261
• InChiKey: AITINBWGCGZTNE-UHFFFAOYSA-N

物化性质

• 沸点：
  330.1±35.0 °C(Predicted)
• 密度：
  1.304±0.06 g/cm3(Predicted)
• 溶解度：
  8.5 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 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：

  2'-甲基-5'-硝基苯甲酰苯胺 在 palladium on activated charcoal 、 氢气 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 生成 N-(3-benzamido-4-methylphenyl)-2,3-dihydro-1,4-benzodioxine-6-carboxamide
  参考文献：
  名称：

  New diarylureas and diarylamides possessing acet(benz)amidophenyl scaffold: Design, synthesis, and antiproliferative activity against melanoma cell line

  摘要：

  A series of new diarylurea and diarylamide derivatives possessing acet(benz)amidophenyl scaffold was synthesized. Their in vitro antiproliferative activity was tested against A375P human melanoma cell line. Compounds 1c,d and 2c,d showed the highest potencies with IC50 values in sub-micromolar scale. In addition, compounds 1b,e,l and 2e,l were more potent than Sorafenib but with IC50 values in micromolar range. Moreover, compound 2c was equipotent to Vemurafenib, and 2d showed higher potency than Vemurafenib against A375P. Molar refractometry calculation and ADME profiling of the highest potent four derivatives 1c,d and 2c,d are also reported. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.03.020
• 作为产物：
  描述：

  苯甲酰氯 、 2-氨基-4-硝基甲苯 在 四丁基溴化铵 、 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 8.0h， 生成 2'-甲基-5'-硝基苯甲酰苯胺
  参考文献：
  名称：

  N-(2-甲基-5-硝基-苯基)苯甲酰胺有机单晶的合成、光谱分析和DFT研究

  摘要：

  N-(2-甲基-5-硝基-苯基)苯甲酰胺(N2M5NPBA)化合物是通过2-甲基-5-硝基苯胺的苯甲酰化合成的。N2M5NPBA 单晶是通过缓慢蒸发技术使用 DMSO 作为溶剂生长的。N2M5NPBA晶体的单晶X射线衍射研究在空间群P 2 1/C下具有单斜晶系，晶格参数a = 4.9490 Å, b = 10.1916 Å, c = 24.969 Å, α = γ = 90°, β = 91 ° 和 V = 1259.1 Å 3. N2M5NPBA 晶体中存在的硝基和酰胺官能团在 FT-IR 光谱表征中得到鉴定。优化了标题分子的分子几何结构，并使用 B3LYP/6-311++G (d, p) 基组通过密度泛函理论 (DFT) 进行了理论分析。N2M5NPBA 的紫外-可见光谱分析预测截止波长为 278 nm（带隙能量 ~4.19 eV）。1小时 & 13C NMR谱记录生长的N2M5NPBA晶体以确认化学结构。生长的

  DOI：

  10.1016/j.molstruc.2021.131172

文献信息

• Amide derivatives
  申请人：Brown S. Dearg

  公开号：US20050245551A1

  公开（公告）日：2005-11-03

  The invention concerns amide derivatives of Formula (Ia) wherein X is —NHCO— or —CONH—; m is 0-3; R 1 is a group such as hydroxy, halogeno, trifluoromethyl, cyano, mercapto, nitro, amino, carboxy and carbamoyl; n is 0-2; R 2 is a group such as hydroxy, halogeno, trifluoromethyl, cyano, mercapto, nitro, amino and carboxy; R 3 is hydrogen, halogeno, (1-6C)alkyl or (1-6C)alkoxy; q is 0-4; and Q is a group such as aryl, aryloxy, aryl-(1-6C)alkoxy, arylamino and N -(1-6C)alkyl-arylamino; or pharmaceutically-acceptable salts or in-vivo-cleavable esters thereof; processes for their preparation, pharmaceutical compositions containing them and their use in the treatment of diseases or medical conditions mediated by cytokines.

  本发明涉及式(Ia)的酰胺衍生物，其中X为—NHCO—或—CONH—；m为0-3；R1为羟基、卤代、三氟甲基、氰基、巯基、硝基、氨基、羧基和氨基甲酰基等基团；n为0-2；R2为羟基、卤代、三氟甲基、氰基、巯基、硝基、氨基和羧基等基团；R3为氢、卤代、(1-6C)烷基或(1-6C)烷氧基；q为0-4；Q为芳基、芳氧基、芳基-(1-6C)烷氧基、芳基氨基和N-(1-6C)烷基-芳基氨基等基团；或其药学上可接受的盐或体内可降解的酯；制备它们的方法、含有它们的制药组合物以及它们在治疗细胞因子介导的疾病或医疗状况中的用途。
• 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：——
• Acylthiourea, Acylurea, and Acylguanidine Derivatives with Potent Hedgehog Inhibiting Activity
  作者：Antonio Solinas、Hélène Faure、Hermine Roudaut、Elisabeth Traiffort、Angèle Schoenfelder、André Mann、Fabrizio Manetti、Maurizio Taddei、Martial Ruat

  DOI：10.1021/jm2013369

  日期：2012.2.23

  The Smoothened (Smo) receptor is the major transducer of the Hedgehog (Hh) signaling pathway. On the basis of the structure of the acylthiourea Smo antagonist (MRT-10), a number of different series of analogous compounds were prepared by ligand-based structural optimization. The acylthioureas, originally identified as actives, were converted into the corresponding acylureas or acylguanidines. In each series, similar structural trends delivered potent compounds with IC50 values in the nanomolar range with respect to the inhibition of the Hh signaling pathway in various cell-based assays and of BODIPY-cyclopamine binding to human Smo. The similarity of their biological activities, in spite of discrete structural differences, may reveal the existence of hydrogen-bonding interactions between the ligands and the receptor pocket. Biological potency of compounds 61, 72, and 86 (MRT-83) were comparable to those of the clinical candidate GDC-0449. These findings suggest that these original molecules will help delineate Smo and Hh functions and can be developed as potential anticancer agents.
• AMIDE DERIVATIVES FOR THE TREATMENT OF DISEASES MEDIATED BY CYTOKINES
  申请人：AstraZeneca AB

  公开号：EP1017378B1

  公开（公告）日：2002-12-11
• BENZAMIDE DERIVATIVES AND THER USE AS CYTOKINE INHIBITORS
  申请人：AstraZeneca AB

  公开号：EP1115707B1

  公开（公告）日：2003-11-12

表征谱图