CAS: 915365-57-0; Cot Inhibitor-1

该化合物是一种双循环芳香化合物,以其生物活动,特别是医药化学活动而闻名.三硝环的存在有助于其作为生物活性分子的潜力,经常与抗微生物学和抗风学特性有关.该物质会增加其结构的多样性,有可能影响其致癌性和光动力学特征.此外,氯和氟基亚基基的出现表明其脂质性会增强,并可能改善化合物与生物目标的结合性.

英文名称Cot Inhibitor-1
中文名称6-[[[1-[2-(氮杂庚烷-1-基)乙基]-1H-1,2,3-三唑-4-基]甲基]氨基]-8-氯-4-[(3-氯-4-氟苯基)氨基]喹啉-3-甲腈
IUPAC名称6-(((1-(2-(azepan-1-yl)ethyl)-1H-1,2,3-triazol-4-yl)methyl)amino)-8-chloro-4-((3-chloro-4-fluorophenyl)amino)quinoline-3-carbonitrile
其它别名8-Chloro-4-[(3-Chloro-4-Fluorophenyl)Amino]-6-[[[1-[2-(Hexahydro-1H-Azepin-1-yl)Ethyl]-1H-1,2,3-Triazol-4-Yl]Methyl]Amino]-3-Quinolinecarbonitrile; 6-[[[1-[2-(Azepan-1-yl)Ethyl]-1H-1,2,3-Triazol-4-Yl]Methyl]Amino]-8-Chloro-4-[(3-Chloro-4-Fluorophenyl)Amino]Quinoline-3-Carbonitrile; Cot Inhibitor-1; 3-Quinolinecarbonitrile, 8-Chloro-4-[(3-Chloro-4-Fluorophenyl)Amino]-6-[[[1-[2-(Hexahydro-1H-Azepin-1-yl)Ethyl]-1H-1,2,3-Triazol-4-Yl]Methyl]Amino]-; 3-Triazol-4-Yl]Methyl]Amino]-; 8-Chloro-4-[(3-Chloro-4-Fluorophenyl)Amino]-6-[[[1-[2-(Hexahydro-1H-Azepin-1-yl)Ethyl]-1H-1; Cot Inhibitor 1,Cot Inhibitor1
CAS编号915365-57-0
MFCD编号:MFCD13184699
分子式:C27H27Cl2FN8分子量:553.47
产品CID: 1952106
产品分类有机原料 → 有机氟化合物 → 氟苯腈系列

相似结构搜索
InChIKey: ZWFKJFUFYPOTKL-UHFFFAOYSA-N
InChI=1S/C27H27Cl2FN8/c28-23-12-19(5-6-25(23)30)34-26-18(14-31)15-33-27-22(26)11-20(13-24(27)29)32-16-21-17-38(36-35-21)10-9-37-7-3-1-2-4-8-37/h5-6,11-13,15,17,32H,1-4,7-
计算化学: 氢键受体数8.0氢键供体数2.0可旋转键数8.0

物理性质

沸点729.961 °C at 760 mmHg
闪点395.267 °C
密度1.42g/cm3
pKa:8.80±0.20(预测)
PSA:94.69
LogP:6.45948
折射率1.692
蒸汽压0 mmHg at 25 °C
溶解性DMSO: 25 mg/mL (45.17 Mm; Need Ultrasonic)H2O: < 0.1 mg/mL (Insoluble)
外观形态淡黄色至黄色粉末
储存条件储存在 -20°C
产品应用该化合物是一种选择性的TPL2脂酶抑制剂(IC50 = 28 NM),抑制人体全血中的TNF-ALPHA生产(IC 50 = 5.7 NM).

MSDS等安全信息

GHS符号GHS07
警示词Warning
危险描述H302-H315-H319-H335
防范说明P261-P280-P301+P312-P302+P352-P305+P351+P338

上下游产品

6-amino-8-chloro-4-((3-chloro-4-fluorophenyl)amino)quinoline-3-carbonitrile

合成工艺路线路线简述

915370-11-5 + 915364-18-0 = 915365-57-0
反应条件:1.1 Reagents: Sodium Triacetoxyborohydride Solvents: 1,2-Dichloroethane; 4 H,Rt
标题:Selective Inhibitors Of Tumor Progression Loci-2 (Tpl2) Kinase With Potent Inhibition Of Tnf-α Production In Human Whole Blood
作者:Wu,Junjun; Et Al
参考文献:Bioorganic & Medicinal Chemistry Letters 日期:2009 卷标:19(13) 页码:3485-3488]

10160-87-9 + 1175146-65-2 = 915365-57-0
反应条件:1.1 Reagents: Sodium Ascorbate,Copper Sulfate1.2 Reagents: Hydrochloric Acid2.1 Reagents: Sodium Triacetoxyborohydride Solvents: 1,2-Dichloroethane; 4 H,Rt
标题:Selective Inhibitors Of Tumor Progression Loci-2 (Tpl2) Kinase With Potent Inhibition Of Tnf-α Production In Human Whole Blood
作者:Wu,Junjun; Et Al
参考文献:Bioorganic & Medicinal Chemistry Letters 日期:2009 卷标:19(13) 页码:3485-3488

📜6-氨基-8-氯-4-[(3-氯-4-氟苯基)氨基]-3-喹啉甲腈,1-[2-(六氢-1H-氮杂革-1-基)乙基]-1H-1,2,3-噻唑-4-羧醛置于三乙酰氧基硼氢化钠体系中,用 1,2-二氯乙烷作为反应溶剂,化学反应 4.0H,反应生成 6-[[[1-[2-(氮杂庚烷-1-基)乙基]-1H-1,2,3-三唑-4-基]甲基]氨基]-8-氯-4-[(3-氯-4-氟苯基)氨基]喹啉-3-甲腈
参考文献:Selective Inhibitors Of Tumor Progression Loci-2 (Tpl2) Kinase With Potent Inhibition Of Tnf-α Production In Human Whole Blood
标题:Selective Inhibitors Of Tumor Progression Loci-2 (Tpl2) Kinase With Potent Inhibition Of Tnf-α Production In Human Whole Blood
摘要:Tpl2 (Cot/map3K8) Is An Upstream Kinase Of Mek In The Erk Pathway. It Plays An Important Role In Tumor Necrosis Factor-Alpha (Tnf-Alpha) Production And Signaling. We Have Discovered That 8-Halo-4-(3-Chloro-4-Fluorophenylamino)-6-[(1H-[1,2,3]Triazol-4-Ylmethyl)-Amino]-Quinoline-3-Carbonitriles (4) Are Potent Inhibitors Of This Enzyme. In Order To Improve The Inhibition Of Tnf-Alpha Production In Lps-Stimulated Human Blood,A Series Of Analogs With A Variety Of Substitutions Around The Triazole Moiety Were Studied. We Found That A Cyclic Amine Group Appended To The Triazole Ring Could Considerably Enhance Potency,Aqueous Solubility,And Cell Membrane Permeability. Optimization Of These Cyclic Amine Groups Led To The Identification Of 8-Chloro-4-(3-Chloro-4-Fluorophenylamino)-6-((1-(1-Ethylpiperidin-4-yl)-1H-1,2,3-Triazol-4-yl) Methylamino)Quinoline-3-Carbonitrile (34). In A Lps-Stimulated Rat Inflammation Model,Compound 34 Showed Good Efficacy In Inhibiting Tnf-Alpha Production. (C) 2009 Elsevier Ltd. All Rights Reserved.
DOI:10.1016/j.Bmcl.2009.05.009

海关参考信息

2903919090-氯苯
2933310010-吡啶
2926909090-其他腈基化合物
2939800000-其他生物碱
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主要参考文献

1. Wu, J., Green, N., Hotchandani, R., et al. Selective inhibitors of tumor progression loci-2 (Tpl2) kinase with potent inhibition of TNF-α production in human whole blood. Bioorg. Med. Chem. Lett. 19(13), 3485-3488 (2009).

合成参考文献

参考文献:10.1124/mol.119.115964
摘要:Lee TD, Lee OW, Brimacombe KR, Chen L, Guha R, Lusvarghi S, Tebase BG, Klumpp-Thomas C, Robey RW, Ambudkar SV, Shen M, Gottesman MM, Hall MD. A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. Molecular Pharmacology. 2019 Nov;96(5):629–40. doi: 10.1124/mol.119.115964.