2-chloro-5-nitro-N-(4-methoxyphenyl)benzamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-chloro-5-nitro-N-(4-methoxyphenyl)benzamide
• 英文别名: 2-chloro-N-(4-methoxyphenyl)-5-nitrobenzamide
• 化学式: C₁₄H₁₁ClN₂O₄
• mdl: MFCD00416630
• 分子量: 306.705
• InChiKey: JNRQZCHUUNJVPB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  84.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-chloro-5-nitro-N-(4-methoxyphenyl)benzamide 在 tin(II) chloride dihdyrate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 六甲基二硅氮烷 作用下， 以 乙醇 、 丙酮 、 乙腈 为溶剂， 反应 4.0h， 生成 N-(N-(4-chloro-3-(4-methoxyphenylcarbamoyl)phenyl)-carbamimidoyl)-3,4,5-trimethoxybenzamide
  参考文献：
  名称：

  Acyl Guanidine Derivatives Modulating The Hedgehog Protein Signaling Pathway

  摘要：

  本发明涉及酰基胍衍生物调节刺猬蛋白信号通路，用作药物，特别用于治疗涉及组织功能障碍的疾病，该功能障碍与刺猬蛋白信号通路的失调有关，以及含有同样物质的药物组合物。本发明还涉及作为新型酰基胍衍生物的物质。

  公开号：

  US20120196865A1
• 作为产物：
  描述：

  2-氯-5-硝基苯甲酸 在 草酰氯 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 生成 2-chloro-5-nitro-N-(4-methoxyphenyl)benzamide
  参考文献：
  名称：

  Acyl Guanidine Derivatives Modulating The Hedgehog Protein Signaling Pathway

  摘要：

  本发明涉及酰基胍衍生物调节刺猬蛋白信号通路，用作药物，特别用于治疗涉及组织功能障碍的疾病，该功能障碍与刺猬蛋白信号通路的失调有关，以及含有同样物质的药物组合物。本发明还涉及作为新型酰基胍衍生物的物质。

  公开号：

  US20120196865A1

文献信息

• Covalent Occlusion of the RORγt Ligand Binding Pocket Allows Unambiguous Targeting of an Allosteric Site
  作者：Femke A. Meijer、Maxime C. M. van den Oetelaar、Richard G. Doveston、Ella N. R. Sampers、Luc Brunsveld

  DOI：10.1021/acsmedchemlett.1c00029

  日期：2021.4.8

  autoimmune diseases, and inhibition of RORγt with small molecules thus holds great potential as a therapeutic strategy. RORγt has a unique allosteric ligand binding site in the ligand binding domain, which is distinct from the canonical, orthosteric binding site. Allosteric modulation of RORγt shows high potential, but the targeted discovery of novel allosteric ligands is highly challenging via currently

  核受体RORγt是T辅助细胞17（Th17）细胞分化和增殖以及促炎性细胞因子（如IL-17a）产生的关键正调控因子。该途径的失调可导致各种自身免疫性疾病的发展，因此用小分子抑制RORγt具有作为治疗策略的巨大潜力。RORγt在配体结合结构域中具有独特的变构配体结合位点，其不同于典型的正构结合位点。RORγt的变构调节显示出很高的潜力，但是通过目前可用的方法，靶向发现新的变构配体具有很高的挑战性。在此，我们介绍RORγt的共价正构化学探针，该探针封闭正构，正构配体的结合，但仍允许变构配体结合。
• Synthesis and Antitumor Activity of Novel Benzophenone Derivatives.
  作者：Eiji KUMAZAWA、Kenji HIROTANI、S. Clifford BURFORD、Keiichi KAWAGOE、Tamotsu MIWA、Ikuo MITSUI、Akio EJIMA

  DOI：10.1248/cpb.45.1470

  日期：——

  Novel benzophenone derivatives were synthesized and screened for cytotoxic and antitumor activity. Friedel-Crafts condensation was employed to construct the benzophenone skeleton. Among the compounds synthesized, morpholino and thiomorpholino benzophenones 3a-d exhibited potent cytotoxic activity against P388 murine leukemia and PC-6 human lung carcinoma cells in vitro, and compounds 3a, 3c, and 3j

  合成了新型的二苯甲酮衍生物，并筛选了其细胞毒性和抗肿瘤活性。使用弗瑞德-克来福特（Friedel-Crafts）缩合反应构建二苯甲酮骨架。在合成的化合物中，吗啉代和硫代吗啉代二苯甲酮3a-d在体外对P388鼠白血病和PC-6人肺癌细胞表现出有效的细胞毒活性，而化合物3a，3c和3j腹膜内给药对它们具有显着的抗肿瘤活性。腹膜内接种小鼠P388细胞引起的恶性腹水。
• One Pot Regioselective Synthesis of a Small Library of Dibenzo[<i>b</i>,<i>f</i>][1,4]thiazepin-11(10<i>H</i>)-ones via Smiles Rearrangement
  作者：Yongmei Zhao、Qiaoling Dai、Zhi Chen、Qihui Zhang、Yongcheng Bai、Chen Ma

  DOI：10.1021/co300139s

  日期：2013.2.11

  A facile and efficient method has been developed for the synthesis of a small library of dibenzo[b,f][1,4]thiazepin-11(10H)-ones via Smiles rearrangement. Compounds were obtained in excellent isolated yields (70%–92%) under metal-free conditions. More specifically, this transition metal-free process relates to an environmentally friendly, economical, and efficient method for preparing benzoic-fused

  已经开发了一种通过Smiles重排合成小的二苯并[ b，f ] [1,4] thiazepin-11（10 H）-ones小型文库的简便有效方法。在无金属条件下，化合物的分离产率极高（70％–92％）。更具体地说，这种无过渡金属的方法涉及制备苯并稠合的七元内酰胺的环保，经济和有效的方法。
• 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.
• Discovery of halo-nitrobenzamides with potential application against human African trypanosomiasis
  作者：Jong Yeon Hwang、David Smithson、Michele Connelly、Julie Maier、Fangyi Zhu、Kiplin R. Guy

  DOI：10.1016/j.bmcl.2009.11.022

  日期：2010.1

  A series of halo-nitrobenzamide were synthesized and evaluated for their ability to block proliferation of Trypanosoma brucei brucei. A number of these compounds had significant activity against the parasite, particularly 2-chloro-N-(4-chlorophenyl)-5-nitrobenzamide 17 which exhibited low micromolar inhibitory potency against T. brucei and selectivity towards both malaria and mammalian cells. (C) 2009 Elsevier Ltd. All rights reserved.