2-(4-Chlorobenzylidene)-6-methylcyclohexanone | 93759-03-6

• 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-(4-Chlorobenzylidene)-6-methylcyclohexanone
• 英文别名: 2-[(4-chlorophenyl)methylidene]-6-methylcyclohexan-1-one
• CAS: 93759-03-6
• 化学式: C₁₄H₁₅ClO
• 分子量: 234.726
• InChiKey: FWDLOXVEAABHRJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(4-Chlorobenzylidene)-6-methylcyclohexanone 在 potassium carbonate 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 14.0h， 生成 4-(3-(4-chlorophenyl)-7-methyl-3,3a,4,5,6,7-hexahydro-2H-indazol-2-yl)-N-(phenylcarbamothioyl)benzenesulfonamide
  参考文献：
  名称：

  Synthesis and in vitro antitumor and antimicrobial activity of some 2,3-diaryl-7-methyl-4,5,6,7-tetrahydroindazole and 3,3a,4,5,6,7-hexahydroindazole derivatives

  摘要：

  The synthesis of a series of 2,3-diaryl-7-methyl-4,5,6,7-tetrahydroindazole and 3,3a, 4,5,6,7-hexahydroindazole derivatives substituted with various biologically-active function groups with anticipated chemotherapeutic activity is described. 4-(7-methyl-3-aryl-3,3a, 4,5,6,7-hexahydro-indazol-2-yl)benzenesulfonamides 2a-c, which were employed as key intermediates in this study, were synthesized by cyclocondensation of 6-arylidene-2-methylcyclohexanones 1a-c with 4-hydrazinobenzenesulfonamide hydrochloride. A detailed discussion of the reactions utilized in the preparation of the intermediate and target compounds is reported, and the structures of the newly synthesized compounds were substantiated with IR, H-1 and C-13 NMR spectral data and elementary microanalyses. Twenty of the newly synthesized compounds were selected by National Cancer Institute (NCI), Maryland, USA, to be evaluated for their antitumor activity and the results revealed that six compounds 3c, 4d, e, 5a, d and 8c exhibited broad spectrum of antitumor activity against most of the tested tumor cell lines. In addition, the in vitro antibacterial and antifungal activities of a number of the target compounds were also tested using the Agar-diffusion method. Some of these compounds have shown significant antibacterial and mild to moderate antifungal activities.

  DOI：

  10.3109/14756366.2011.653354
• 作为产物：
  描述：

  4-氯苯甲醛 、 2-甲基环己酮 在 potassium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 生成 2-(4-Chlorobenzylidene)-6-methylcyclohexanone
  参考文献：
  名称：

  新型四氢喹唑啉胺作为选择性组胺3受体拮抗剂治疗肥胖症。

  摘要：

  组胺3受体（H3R）是一种突触前受体，可调节多种神经递质，包括组胺和各种基本生理过程，如进食，唤醒，认知和疼痛。H3R被认为是治疗几种中枢神经系统疾病的药物靶标。我们已经合成和鉴定了一系列新型的4-芳基-6-甲基-5,6,7,8-四氢喹唑啉胺，它们可以作为选择性的H3R拮抗剂。在所有合成的化合物中，体外和对接研究表明，4-甲氧基-苯基取代的四氢喹唑啉胺化合物4c具有有效和选择性的H3R拮抗剂活性（IC50 <0.04μM）。化合物4c对hERG离子通道未显示任何活性，且泛测定干扰化合物的责任。药代动力学研究表明4c穿越了血脑屏障，而体内研究表明4c诱导了肥胖症的厌食症和体重减轻，但对瘦小鼠却没有。这些数据通过拮抗H3R揭示了4c作为抗肥胖候选药物的治疗潜力。

  DOI：

  10.1021/acs.jmedchem.9b00241

文献信息

• Fungicidal compositions containing (benzylidene)-azolymethylcycloalkane
  申请人：Rhone-Poulenc Agrochimie

  公开号：US05380743A1

  公开（公告）日：1995-01-10

  (Benzylidene)-azolylmethylcycloalkane or -alkene of formula ##STR1## in which: A and A.sub.1 are hydrocarbon chains of 1 to 3 carbon atoms, R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 are hydrocarbon radicals, X is halogen, Y is H or halogen, n=1, 2 or 3, W is --CH.dbd. or --N.dbd.. Use as a fungicide.

  (Benzylidene)-azolylmethylcycloalkane或-alkene的化学式为##STR1##其中：A和A.sub.1是1至3个碳原子的碳氢链，R.sub.1，R.sub.2，R.sub.3，R.sub.4和R.sub.5是碳氢基，X是卤素，Y是H或卤素，n = 1、2或3，W是--CH.dbd.或--N.dbd.。用作杀菌剂。
• Intermediate compounds useful in the preparation of fungicidal
  申请人：Rhone-Poulenc Agrochimie

  公开号：US05639918A1

  公开（公告）日：1997-06-17

  (Benzylidene)-azolylmethylcycloalkane or -alkene of formula ##STR1## in which: A and A.sub.1 are hydrocarbon chains of 1 to 3 carbon atoms, R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 are hydrocarbon radicals, X is halogen, Y is H or halogen, n=1, 2 or 3, W is --CH.dbd. or --N.dbd.. Use as a fungicide.

  公式为##STR1##的(Benzylidene)-azolylmethylcycloalkane或-alkene，其中：A和A.sub.1是1至3个碳原子的碳氢链，R.sub.1，R.sub.2，R.sub.3，R.sub.4和R.sub.5是碳氢基团，X是卤素，Y是H或卤素，n = 1，2或3，W是-CH.dbd.或-N.dbd.。用作杀真菌剂。
• Fungicidal compositions containing (benzylidene)-azolylmethylcycloalkane
  申请人：Rhone-Poulenc Agrochimie

  公开号：US05256683A1

  公开（公告）日：1993-10-26

  (Benzylidene)-azolylmethylcycloalkane or -alkene of formula ##STR1## in which: A and A.sub.1 are hydrocarbon chains of 1 to 3 carbon atoms, R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 are hydrocarbon radicals, X is halogen, Y is H or halogen, n=1, 2 or 3, W is --CH.dbd. or --N.dbd.. Use as a fungicide.

  (Benzylidene)-azolylmethylcycloalkane或-烯的化学式为##STR1##其中：A和A.sub.1是1至3个碳原子的碳氢链，R.sub.1、R.sub.2、R.sub.3、R.sub.4和R.sub.5是碳氢基团，X是卤素，Y是H或卤素，n=1、2或3，W为--CH.dbd.或--N.dbd.。用作杀真菌剂。
• Novel Tetrahydroquinazolinamines as Selective Histamine 3 Receptor Antagonists for the Treatment of Obesity
  作者：Ajeet Kumar、Venkata Reddy Pasam、Ravi Kumar Thakur、Maninder Singh、Kartikey Singh、Mahendra Shukla、Anubhav Yadav、Shalini Dogra、Chandan Sona、Deepmala Umrao、Swati Jaiswal、Hafsa Ahmad、Mamunur Rashid、Sandeep K. Singh、Muhammad Wahajuddin、Anil Kumar Dwivedi、Mohammad Imran Siddiqi、Jawahar Lal、Rama Pati Tripathi、Prem N. Yadav

  DOI：10.1021/acs.jmedchem.9b00241

  日期：2019.5.9

  as selective H3R antagonists. Among all the synthesized compounds, in vitro and docking studies suggested that the 4-methoxy-phenyl-substituted tetrahydroquinazolinamine compound 4c has potent and selective H3R antagonist activity (IC50 < 0.04 μM). Compound 4c did not exhibit any activity on the hERG ion channel and pan-assay interference compounds liability. Pharmacokinetic studies showed that 4c crosses

  组胺3受体（H3R）是一种突触前受体，可调节多种神经递质，包括组胺和各种基本生理过程，如进食，唤醒，认知和疼痛。H3R被认为是治疗几种中枢神经系统疾病的药物靶标。我们已经合成和鉴定了一系列新型的4-芳基-6-甲基-5,6,7,8-四氢喹唑啉胺，它们可以作为选择性的H3R拮抗剂。在所有合成的化合物中，体外和对接研究表明，4-甲氧基-苯基取代的四氢喹唑啉胺化合物4c具有有效和选择性的H3R拮抗剂活性（IC50 <0.04μM）。化合物4c对hERG离子通道未显示任何活性，且泛测定干扰化合物的责任。药代动力学研究表明4c穿越了血脑屏障，而体内研究表明4c诱导了肥胖症的厌食症和体重减轻，但对瘦小鼠却没有。这些数据通过拮抗H3R揭示了4c作为抗肥胖候选药物的治疗潜力。
• Synthesis and <i>in vitro</i> antitumor and antimicrobial activity of some 2,3-diaryl-7-methyl-4,5,6,7-tetrahydroindazole and 3,3a,4,5,6,7-hexahydroindazole derivatives
  作者：Hassan M. Faidallah、Khalid A. Khan、Sherif A. F. Rostom、Abdullah M. Asiri

  DOI：10.3109/14756366.2011.653354

  日期：2013.6.1

  The synthesis of a series of 2,3-diaryl-7-methyl-4,5,6,7-tetrahydroindazole and 3,3a, 4,5,6,7-hexahydroindazole derivatives substituted with various biologically-active function groups with anticipated chemotherapeutic activity is described. 4-(7-methyl-3-aryl-3,3a, 4,5,6,7-hexahydro-indazol-2-yl)benzenesulfonamides 2a-c, which were employed as key intermediates in this study, were synthesized by cyclocondensation of 6-arylidene-2-methylcyclohexanones 1a-c with 4-hydrazinobenzenesulfonamide hydrochloride. A detailed discussion of the reactions utilized in the preparation of the intermediate and target compounds is reported, and the structures of the newly synthesized compounds were substantiated with IR, H-1 and C-13 NMR spectral data and elementary microanalyses. Twenty of the newly synthesized compounds were selected by National Cancer Institute (NCI), Maryland, USA, to be evaluated for their antitumor activity and the results revealed that six compounds 3c, 4d, e, 5a, d and 8c exhibited broad spectrum of antitumor activity against most of the tested tumor cell lines. In addition, the in vitro antibacterial and antifungal activities of a number of the target compounds were also tested using the Agar-diffusion method. Some of these compounds have shown significant antibacterial and mild to moderate antifungal activities.