4-chloro-N-<(benzotriazol-1-yl)methyl>aniline | 62001-32-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并三唑类
• 英文名称: 4-chloro-N-<(benzotriazol-1-yl)methyl>aniline
• 英文别名: N-((1H-benzo[d][1,2,3]triazol-1-yl)methyl)-4-chloroaniline；N-((1H-benzo[d][1,2,3]triazole)-1-methyl)-4-chloroaniline；N-benzotriazol-1-ylmethyl-4-chloro-aniline；N-(1H-benzotriazol-1-ylmethyl)-4-chloroaniline；N-(benzotriazol-1-ylmethyl)-4-chloroaniline
• CAS: 62001-32-5
• 化学式: C₁₃H₁₁ClN₄
• mdl: MFCD00451363
• 分子量: 258.71
• InChiKey: PHAXIVPIOCGFIQ-UHFFFAOYSA-N

物化性质

• 熔点：
  164 °C(Solv: ethanol (64-17-5))
• 沸点：
  497.6±25.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  42.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-chloro-N-<(benzotriazol-1-yl)methyl>aniline 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以80%的产率得到4-氯-N-甲基苯胺
  参考文献：
  名称：

  Katritzky, Alan R.; Rachwal, Stanislaw; Rachwal, Bogumila, Journal of the Chemical Society. Perkin transactions I, 1987, p. 805 - 810

  摘要：

  DOI：
• 作为产物：
  描述：

  1H-苯并三唑-1-甲醇 、 对氯苯胺 以 乙醇 为溶剂， 以47%的产率得到4-chloro-N-<(benzotriazol-1-yl)methyl>aniline
  参考文献：
  名称：

  Milata; Kada; Zalibera, Bollettino Chimico Farmaceutico, 2001, vol. 140, # 4, p. 215 - 220

  摘要：

  DOI：

文献信息

• 苯并三氮唑衍生物做为RSK2抑制剂的合成及应 用
  申请人：华东理工大学

  公开号：CN102688233B

  公开（公告）日：2016-02-17

  发明涉及苯并三氮唑衍生物的合成及其用途。具体而言，本发明涉及下式II所示的化合物、含有式II化合物的药物组合物及所述化合物在制备治疗或预防RSK2介导的疾病用的药物中的用途：
• Design, synthesis, and biological evaluation of novel 4,4‐difluoro‐1‐methyl‐ <i>N</i> , 6‐diphenyl‐5, 6‐dihydro‐4 <i>H</i> ‐pyrimido [4, 5‐ <i>b</i> ] [1, 2, 4] triazolo [4, 3‐ <i>d</i> ] [1, 4] diazepin‐8‐amine derivatives as potential BRD4 inhibitors
  作者：Jiuhui Li、Wenjie Zhang、Qianqian Qiu、Daoguang Zhou、Ziying Feng、Zhenzhen Tong、Jiaxin Wei、Wenlong Huang、Jieming Li、Hai Qian、Wei Shi

  DOI：10.1111/cbdd.13833

  日期：2021.5

  inhibitors can effectively inhibit the proliferation of tumor cells. By taking BI‐2536 (PLK1 and BRD4 inhibitor) as the lead compound, sixteen novel BRD4 inhibitors with the 4,4‐difluoro‐1‐methyl‐N,6‐diphenyl‐5,6‐dihydro‐4H‐pyrimido[4,5‐b] [1,2,4] triazolo[4,3‐d] [1,4] diazepine‐8‐amine structure were designed and synthetized. Among the target compounds, compound 15h exhibited outstanding inhibition for

  含溴结构域蛋白4（BRD4）在癌症中起着极其重要的生理作用，而BRD4抑制剂可以有效抑制肿瘤细胞的增殖。以BI-2536（PLK1和BRD4抑制剂）为先导化合物，开发了十六种新型BRD4抑制剂，分别带有4,4-二氟-1-甲基-N，6-二苯基-5,6-二氢-4 H-嘧啶基[4]。 ，5- b ] [1,2,4]三唑并[4,3- d ] [1,4]二氮杂-8-胺结构被设计并合成。在目标化合物中，化合物15h在BRD4-BD1抑制活性测定中表现出对BRD4-BD1的出色抑制作用（IC 50值为0.42μM）。此外，细胞生长抑制试验证明化合物15h有效抑制MV4-11细胞的增殖（IC 50值为0.51μM ）。此外，化合物15h可有效诱导MV4-11白血病细胞凋亡和G0 / G1周期阻滞，并以剂量​​依赖性方式下调c-Myc的表达。综上所述，最佳化合物15h有望成为进一步研究的临床治疗药物。
• Triazole and Benzotriazole Derivatives as Novel Inhibitors for p90 Ribosomal S6 Protein Kinase 2: Synthesis, Molecular Docking and SAR Analysis
  作者：Jun Yuan、Ye Zhong、Shiliang Li、Xue Zhao、Guoqin Luan、Zhenjiang Zhao、Jin Huang、Honglin Li、Yufang Xu

  DOI：10.1002/cjoc.201300443

  日期：2013.7.19

  series of triazole and benzotriazole derivatives as novel p90 ribosomal S6 protein kinase 2 (RSK2) inhibitors were designed and synthesized. The in vitro activities against RSK2 were evaluated, and among 14 compounds, compounds 5, 6, 11, 12, 13 and 14 exhibited enzyme IC50 values of 8.91, 2.86, 3.19, 3.05, 4.49 and 2.09 µmol/L respectively. The proposed binding modes were simulated using molecular docking

  设计并合成了一系列三唑和苯并三唑衍生物，作为新型的p90核糖体S6蛋白激酶2（RSK2）抑制剂。在体外对RSK2活动进行了评价，并且其中14个化合物，化合物5，6，11，12，13和14显示出酶IC 50分别为8.91、2.86、3.19、3.05、4.49和2.09 µmol / L。使用分子对接方法模拟了拟议的结合模式，对接结果与结构-活性关系（SAR）分析表明，所有这些活性化合物均与NTKD上的RSK2 ATP结合位点结合，并且在电子对上具有电子给体基团。苯基的4-位是抑制活性的决定点。
• Synthesis of α-Amino Unsymmetrical Diorganyl Selenides via Novel Synthetic Auxiliary Benzotriazole Promoted by Samarium Dhodide
  作者：Weiliang Bao、Yongmin Zhang、Jianqing Zhou、Yunfa Zheng

  DOI：10.1080/00397919608004637

  日期：1996.9

  Abstract α -Amino unsymmetrical diorganyl selenides are synthesized through nucleophilic substitution of a benzotriazolate anion by selenolates promoted by samarium diiodide.

  摘要 α-氨基不对称二有机硒化物是通过二碘化钐促进的硒化物对苯并三唑阴离子进行亲核取代而合成的。
• Tyrosine Kinase Inhibitors. 3. Structure-Activity Relationships for Inhibition of Protein Tyrosine Kinases by Nuclear-Substituted Derivatives of 2,2'-Dithiobis(1-methyl-N-phenyl-1H-indole-3-carboxamide)
  作者：Gordon W. Rewcastle、Brian D. Palmer、Ellen M. Dobrusin、David W. Fry、Alan J. Kraker、William A. Denny

  DOI：10.1021/jm00039a016

  日期：1994.6

  A series of indole-substituted 2,2'-dithiobis(1-methyl-N-phenyl-1H-indole-3-carboxamides) were prepared and evaluated for their ability to inhibit the tyrosine kinase activity of both the epidermal growth factor receptor (EGFR) and the nonreceptor pp60(v-src) tyrosine kinase. The compounds were synthesized by conversion of appropriate 1-methyloxindoles to 1-methyl-2-indolinethiones with P2S5 followed by subsequent reaction with NaH and phenyl isocyanate and oxidative dimerization of the resulting 2,3-dihydro-N-phenyl-2-thioxo-1H-indole-3-carboxamides. The parent compound and many of the substituted analogues were moderately potent inhibitors of both kinase enzymes, but no clear relationships were seen between substitution on the indole ring and inhibitory activity, While 4-substituted compounds were generally inactive, 5-substituted derivatives with electron-withdrawing groups showed inhibitory activity. However, none of the substituted compounds showed significantly better activity than the unsubstituted parent compound. There was generally a good correlation between activity against the EGFR and pp60(v-src) kinases, but several compounds did show some specificity (>20-fold) of inhibition; 5-Cl and 5-Br derivatives preferentially inhibited pp60(v-src), while the 5-CF3 compound preferentially inhibited EGFR. Selected compounds from the series were found to inhibit the growth of Swiss 3T3 fibroblasts with IC(50)s in the range 2-25 mu M, the most active being 4-substituted derivatives. The compounds inhibited bFGF-mediated protein tyrosine phosphorylation in intact cells more effectively than EGFR- or PDGF-mediated phosphorylation.