N-[5-bromo-2-methyloxy-3-pyridinyl]-4-chlorophenylsulfonamide | 1425046-28-1

• 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: N-[5-bromo-2-methyloxy-3-pyridinyl]-4-chlorophenylsulfonamide
• 英文别名: N-(5-bromo-2-methoxypyridin-3-yl)-4-chlorobenzenesulfonamide
• CAS: 1425046-28-1
• 化学式: C₁₂H₁₀BrClN₂O₃S
• 分子量: 377.646
• InChiKey: HKUOVBSQEQHFNX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  76.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-[5-bromo-2-methyloxy-3-pyridinyl]-4-chlorophenylsulfonamide 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 potassium acetate 、 sodium carbonate 作用下， 以 乙二醇二甲醚 、 乙醇 、 水 为溶剂， 反应 5.0h， 生成 N-(7-(6-methoxy-5-(4-chlorophenylsulfonamido)pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)acetamide
  参考文献：
  名称：

  Synthesis and anticancer activity evaluation of a series of [1,2,4]triazolo[1,5-a]pyridinylpyridines in vitro and in vivo

  摘要：

  A series of [1,2,4]triazolo[1,5-a]pyridinylpyridines were synthesized and characterized. Their antiproliferative activities in vitro were evaluated by MTT against three human cancer cell lines including HCT-116, U-87 MG and MCF-7 cell lines. The SAR of target compounds was preliminarily discussed. The compounds 1c and 2d with potent antiproliferative activities were tested for their effects on the AKT and p-AKT(473). The anticancer effect of 1c was evaluated in mice bearing sarcoma S-180 model. The results suggest that the title compounds are potent anticancer agents. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.06.052
• 作为产物：
  描述：

  5-溴-2-甲氧基-3-硝基砒啶 在 吡啶 、 盐酸 、 tin(II) chloride dihdyrate 作用下， 生成 N-[5-bromo-2-methyloxy-3-pyridinyl]-4-chlorophenylsulfonamide
  参考文献：
  名称：

  Synthesis and anticancer activity evaluation of a series of [1,2,4]triazolo[1,5-a]pyridinylpyridines in vitro and in vivo

  摘要：

  A series of [1,2,4]triazolo[1,5-a]pyridinylpyridines were synthesized and characterized. Their antiproliferative activities in vitro were evaluated by MTT against three human cancer cell lines including HCT-116, U-87 MG and MCF-7 cell lines. The SAR of target compounds was preliminarily discussed. The compounds 1c and 2d with potent antiproliferative activities were tested for their effects on the AKT and p-AKT(473). The anticancer effect of 1c was evaluated in mice bearing sarcoma S-180 model. The results suggest that the title compounds are potent anticancer agents. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.06.052

文献信息

• Quinazolinone Compound and Application Thereof
  申请人：LUOXIN PHARMACEUTICAL (SHANGHAI) CO., LTD.

  公开号：US20200317660A1

  公开（公告）日：2020-10-08

  The present invention relates to a series of quinazolinone compounds and applications thereof as PI3Kα inhibitors. In particular, the present invention relates to a compound shown in formula (I) and a tautomer or pharmaceutically acceptable salt thereof.

  本发明涉及一系列喹唑啉酮化合物及其作为PI3Kα抑制剂的应用。具体而言，本发明涉及一种在式（I）中显示的化合物及其互变异构体或药用可接受的盐。
• QUINAZOLINONE COMPOUND AND APPLICATION THEREOF
  申请人：Luoxin Pharmaceutical (Shanghai) Co., Ltd.

  公开号：EP3712143A1

  公开（公告）日：2020-09-23

  The present invention relates to a series of quinazolinone compounds and applications thereof as PI3Kα inhibitors. In particular, the present invention relates to a compound shown in formula (I) and a tautomer or pharmaceutically acceptable salt thereof.

  本发明涉及一系列喹唑啉酮化合物及其作为 PI3Kα 抑制剂的应用。特别是，本发明涉及式（I）所示的化合物及其同系物或药学上可接受的盐。
• Synthesis and antitumor activity evaluation of PI3K inhibitors containing 3-substituted quinazolin-4(3H)-one moiety
  作者：Hao Zhang、Min-Hang Xin、Xiao-Xiao Xie、Shuai Mao、Sai-Jie Zuo、She-Min Lu、San-Qi Zhang

  DOI：10.1016/j.bmc.2015.11.027

  日期：2015.12

  In present study, a series of N-(2-methoxy-5-(3-substituted quinazolin-4(3H)-one-6-yl)-pyridin-3-yl) phenylsulfonamide were synthesized. Their antiproliferative activities in vitro were evaluated via MTT assay against HCT116 and MCF-7 cancer cell lines. The SAR of title compounds was discussed. The compounds (S)-C5 and (S)-C8 displayed potent inhibitory activity against PI3Ks and mTOR, especially against PI3K alpha. In addition, compound (S)-C5 can efficaciously inhibit tumor growth in a mice S-180 model. These findings suggest that our designed compounds can serve as potent PI3K inhibitors and effective anticancer agents. (c) 2015 Published by Elsevier Ltd.
• Modification of N -(6-(2-methoxy-3-(4-fluorophenylsulfonamido)pyridin-5-yl)-[1,2,4]triazolo[1,5- a ]pyridin-2-yl)acetamide as PI3Ks inhibitor by replacement of the acetamide group with alkylurea
  作者：Xiao-Meng Wang、Shuai Mao、Lei Cao、Xiao-Xiao Xie、Min-Hang Xin、Jia-Fang Lian、Yong-Xiao Cao、San-Qi Zhang

  DOI：10.1016/j.bmc.2015.07.017

  日期：2015.9

  N-(6-(2-Methoxy-3-(4-fluorophenylsulfonamido)pyridin-5-yl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)acetamide exhibits remarkable anticancer effects and toxicity when orally administrated. In present study, alkylurea moiety replaced the acetamide group in the compound and a series of 1-alkyl-3-(6-(2-methoxy-3-sulfonylaminopyridin-5-yl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl) urea derivatives were synthesized. The antiproliferative activities of the synthesized compounds in vitro were evaluated against four human cancer cell lines. Several compounds with potent antiproliferative activities were tested for their acute oral toxicity and their inhibitory activity against PI3Ks and mTOR. The results indicate that the compound attached a alkylurea or 2-(dialkylamino)ethylurea moiety at the 2-position of [1,2,4]triazolo[1,5-a]pyridine can retain the antiproliferative activity and the inhibitory activity against PI3Ks and mTOR. In addition, their acute oral toxicity reduced dramatically. Moreover, the results also indicate that compound 1e can efficaciously inhibit tumor growth in a mice S180 model. These findings suggest that title compounds can serve as potent PI3K inhibitors and effective anticancer agents with low toxicity. (C) 2015 Elsevier Ltd. All rights reserved.