4-amino-4'-chlorodiphenylmethane | 50275-07-5

• 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: 4-amino-4'-chlorodiphenylmethane
• 英文别名: 4-(4-chloro-benzyl)-aniline；4-(4-Chlor-benzyl)-anilin；4-(4'-chlorophenylmethyl)-aniline；4-(4-Chlorobenzyl)aniline；4-[(4-chlorophenyl)methyl]aniline
• CAS: 50275-07-5
• 化学式: C₁₃H₁₂ClN
• 分子量: 217.698
• InChiKey: XBWJBPNVDRSJCK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  26
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-amino-4'-chlorodiphenylmethane 在 硫酸 、 苯 作用下， 生成 6-(4-chloro-benzyl)-4-methyl-quinolin-2-ol
  参考文献：
  名称：

  Substituted Quinolines^1,2

  摘要：

  DOI：

  10.1021/ja01190a039
• 作为产物：
  描述：

  1-chloro-4-(4-nitrobenzyl)benzene 在 溶剂黄146 、 锌 作用下， 反应 0.5h， 生成 4-amino-4'-chlorodiphenylmethane
  参考文献：
  名称：

  Quinolone Carboxylic Acids as a Novel Monoketo Acid Class of Human Immunodeficiency Virus Type 1 Integrase Inhibitors

  摘要：

  Human immunodeficiency virus type 1 (HIV-1) integrase is a crucial target for antiretroviral drugs, and several keto-enol acid class (often referred to as diketo acid class) inhibitors have clinically exhibited marked antiretroviral activity. Here, we show the synthesis and the detailed structure-activity relationship of the quinolone carboxylic acids as a novel monoketo acid class of integrase inhibitors. 6-(3-Chloro-2-fluorobenzyl)- 1-((2,S)-1-hydroxy-3,3-dimethylbutan-2-yl)-7-methoxy-4-oxo- 1,4-dihydroquinoline-3-carboxylic acid 51, which showed an IC50 of 5.8 nM in the strand transfer assay and an ED50 of 0.6 nM in the antiviral assay, and 6-(3-chloro-2-fluorobenzyl)-1-((2S)-1-hydroxy-3-methylbutan-2-yl)-7-methoxy-4-oxo-4-dihydroquinoline-3-carboxylic acid 49, which had an IC50 of 7.2 nM and an ED50 of 0.9 nM, were the most potent compounds in this class. The monoketo acid 49 was much more potent at inhibiting integrase-catalyzed strand transfer processes than 3'-processing reactions, as is the case with the keto-enol acids. Elvitegravir 49 was chosen as a candidate for further studies and is currently in phase 3 clinical trials.

  DOI：

  10.1021/jm900460z

文献信息

• Further exploration of the structure-activity relationship of dual soluble epoxide hydrolase/fatty acid amide hydrolase inhibitors
  作者：Stephanie Wilt、Sean Kodani、Leah Valencia、Paula K. Hudson、Stephanie Sanchez、Taylor Quintana、Christophe Morisseau、Bruce D. Hammock、Ram Kandasamy、Stevan Pecic

  DOI：10.1016/j.bmc.2021.116507

  日期：2021.12

  tolerated by both enzymes, producing excellent inhibition potencies in the low nanomolar range (e.g. 6o, sEH IC50 = 2.5 nM; FAAH IC50 = 9.8 nM). Docking experiments show that the new class of dual inhibitors bind within the catalytic sites of both enzymes. Prediction of several pharmacokinetic/pharmacodynamic properties suggest that these new dual inhibitors are good candidates for further in vivo evaluation

  脂肪酸酰胺水解酶 (FAAH) 是一种膜蛋白，可水解内源性大麻素，抑制其产生镇痛和抗炎作用。可溶性环氧化物水解酶 (sEH) 将环氧二十碳三烯酸 (EET) 水解为二羟基二十碳四烯酸。EET 具有抗炎和消炎的特性，因此抑制 sEH 可减少炎症。同时抑制这两种酶可能代表一种治疗慢性疼痛的新方法。与具有单一靶点的配体相比，具有多个靶点的药物可以提供更好的治疗效果并减少副作用。以前，采用微波辅助方法合成苯并噻唑类似物的文库，从中可以得到高亲和力的双重抑制剂（例如3、sEH IC50  = 9.6 纳米；FAAH IC 50  = 7 nM) 被确定。在这里，我们的结构-活性关系研究表明，4-苯基噻唑部分对这两种酶具有良好的耐受性，在低纳摩尔范围内产生出色的抑制效力（例如6o，sEH IC 50  = 2.5 nM；FAAH IC 50  = 9.8 nM）。对接实验表明，新型双重抑制剂结合在两种
• Practical Route to 2-Quinolinones via a Pd-Catalyzed C–H Bond Activation/C–C Bond Formation/Cyclization Cascade Reaction
  作者：Junliang Wu、Shaohua Xiang、Jing Zeng、Minli Leow、Xue-Wei Liu

  DOI：10.1021/ol503292p

  日期：2015.1.16

  Quinolinone derivatives were constructed via a Pd-catalyzed C–H bond activation/C–C bond formation/cyclization cascade process with simple anilines as the substrates. This finding provides a practical procedure for the synthesis of quinolinone-containing alkaloids and drug molecules. The utility of this method was demonstrated by a formal synthesis of Tipifarnib.

  喹啉酮衍生物是通过Pd催化的C–H键活化/ CC键形成/环化级联过程构建的，并以简单的苯胺为底物。该发现为合成含喹啉酮的生物碱和药物分子提供了实用的程序。蒂法法尼的正式合成证明了该方法的实用性。
• Etude sur les cétones quinoléiques I
  作者：Henri De Diesbach、André Pugin、François Morard、Wojciech Nowaczinski、Joseph Dessibourg

  DOI：10.1002/hlca.19520350718

  日期：1952.12.1

  Dans ce travail on étudie:

  Dans ce在étudie上的旅行：
• N-phenyl-2-cyano-3-hydroxy-propenamides
  申请人：Roussel Uclaf

  公开号：US05416112A1

  公开（公告）日：1995-05-16

  A compound selected from the group consisting of a compound of the formula ##STR1## wherein R.sub.1 is selected from the group consisting of alkyl of 1 to 6 carbon atoms, cycloalkyl of 3 to 6 carbon atoms and alkenyl and alkynyl of 2 to 6 carbon atoms, R.sub.2 is hydrogen or alkyl of 1 to 3 carbon atoms, Y is selected from the group consisting of ##STR2## Z.sub.1 and Z.sub.2 are individually selected from the group consisting of hydrogen, halogen, --NO.sub.2, --CN and alkyl of 1 to 3 carbon atoms, R.sub.3 is hydrogen or alkyl of 1 to 3 carbon atoms, m is an integer from 0 to 6, R.sub.4, R.sub.5, R.sub.6, R.sub.7 and R.sub.8 are individually selected from the group consisting of hydrogen, halogen, --CN, --NO.sub.2, alkyl, alkylthio and alkoxy of 1 to 6 carbon atoms, cycloalkyl of 3 to 6 carbon atoms, --COR.sub.10, --(CH.sub.2).sub.n --CX.sub.3, --O--(CH.sub.2).sub.n CX.sub.3 and --S--(CH.sub.2).sub.n --CX.sub.3, R.sub.10 is selected from the group consisting of hydrogen, alkyl of 1 to 6 carbon atoms and cycloalkyl of 3 to 6 carbon atoms, n is an integer from 0 to 3, X is halogen or R.sub.6 and R.sub.7 together form --O--CH.sub.2 --O-- and their non-toxic, pharmaceutically acceptable salts with a base having anti-inflammatory and immunomodulatory activity.

  从以下化合物中选择的一种化合物，其中R.sub.1从1到6个碳原子的烷基、3到6个碳原子的环烷基和2到6个碳原子的烯基和炔基组成的群组中选择，R.sub.2是氢或1到3个碳原子的烷基，Y从以下组成的群组中选择##STR2## Z.sub.1和Z.sub.2分别从氢、卤素、--NO.sub.2、--CN和1到3个碳原子的烷基组成的群组中选择，R.sub.3是氢或1到3个碳原子的烷基，m是从0到6的整数，R.sub.4、R.sub.5、R.sub.6、R.sub.7和R.sub.8分别从氢、卤素、--CN、--NO.sub.2、烷基、烷基硫和1到6个碳原子的烷氧基、3到6个碳原子的环烷基、--COR.sub.10、--(CH.sub.2).sub.n --CX.sub.3、--O--(CH.sub.2).sub.n CX.sub.3和--S--(CH.sub.2).sub.n --CX.sub.3组成的群组中选择，R.sub.10从1到6个碳原子的烷基和3到6个碳原子的环烷基组成的群组中选择，n是从0到3的整数，X是卤素或R.sub.6，R.sub.7共同形成--O--CH.sub.2 --O--的群组，以及具有抗炎和免疫调节活性的非毒性、药学上可接受的碱盐。
• N-((1-BENZYL-1H-1,2,3-TRIAZOL-4-YL)METHYL)ARYLAMIDE COMPOUNDS AS POTENTIAL ANTICANCER AGENTS AND A PROCESS FOR THE PREPARATION THEREOF
  申请人：COUNCIL OF SCIENTIFIC & INDUSTRIAL RESEARCH

  公开号：US20150166507A1

  公开（公告）日：2015-06-18

  The present invention provides a compound of general formula 1, useful as potential anticancer agents against human cancer cell lines and process for the preparation thereof. R 1 =H, 4-F, 4-Cl, 4-Br, 4-OMe, 3-F, 2,4-diOMe, 2,5-diOMe, 3,5-diOMe, 3,4,5-triOMe, 4-ClBn R 2 =3-OPh, 4-F, 4-Cl, 4-Br, 4-OMe, 3,5-diOMe

  本发明提供了一种通用式1的化合物，可作为潜在的抗癌剂用于对抗人类癌细胞系，并提供其制备方法。R1=H, 4-F, 4-Cl, 4-Br, 4-OMe, 3-F, 2,4-diOMe, 2,5-diOMe, 3,5-diOMe, 3,4,5-triOMe, 4-ClBnR2=3-OPh, 4-F, 4-Cl, 4-Br, 4-OMe, 3,5-diOMe