3,4-dichloro-N-[3-(2,5-dimethylbenzyloxy)-4-(N-methanesulfonyl-N-methylamino)phenyl]benzamide | 1357168-33-2

• 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: 3,4-dichloro-N-[3-(2,5-dimethylbenzyloxy)-4-(N-methanesulfonyl-N-methylamino)phenyl]benzamide
• 英文别名: 3,4-dichloro-N-[3-(2,5-dimethyl-benzyloxy)-4-(methanesulfonyl-methyl-amino)-phenyl]-benzamide；3,4-dichloro-N-[3-[(2,5-dimethylphenyl)methoxy]-4-[methyl(methylsulfonyl)amino]phenyl]benzamide
• CAS: 1357168-33-2
• 化学式: C₂₄H₂₄Cl₂N₂O₄S
• 分子量: 507.438
• InChiKey: XHTXRYVLZNPDSU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  84.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2,5-二甲基苄氯 在 iron(III) chloride 、 水 、 sodium hydride 、 potassium carbonate 、 sodium hydroxide 、 锌 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 生成 3,4-dichloro-N-[3-(2,5-dimethylbenzyloxy)-4-(N-methanesulfonyl-N-methylamino)phenyl]benzamide
  参考文献：
  名称：

  From COX-2 inhibitor nimesulide to potent anti-cancer agent: Synthesis, in vitro, in vivo and pharmacokinetic evaluation

  摘要：

  Cyclooxygenase-2 (COX-2) inhibitor nimesulide inhibits the proliferation of various types of cancer cells mainly via COX-2 independent mechanisms, which makes it a good lead compound for anti-cancer drug development. In the presented study, a series of new nimesulide analogs were synthesized based on the structure function analysis generated previously. Some of them displayed very potent anti-cancer activity with IC(50)s around 100 nM-200 nM to inhibit SKBR-3 breast cancer cell growth. CSUOH0901 (NSC751382) from the compound library also inhibits the growth of the 60 cancer cell lines used at National Cancer Institute Developmental therapeutics Program (NCIDTP) with IC(50)s around 100 nM-500 nM. Intraperitoneal injection with a dosage of 5 mg/kg/d of CSUOH0901 to nude mice suppresses HT29 colorectal xenograft growth. Pharmacokinetic studies demonstrate the good bioavailability of the compound. Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2011.11.012

文献信息

• AMIDE DERIVATIVES OF BENZENE-SULFONANILIDE, PHARMACEUTICAL COMPOSITION THEREOF AND METHOD FOR CANCER TREATMENT USING THE SAME
  申请人：Su Bin

  公开号：US20120095092A1

  公开（公告）日：2012-04-19

  The invention provides a compound of formula (I), a pharmaceutical composition thereof, a method of preparing a medicament for the treatment of a cancer, and a method of treating cancers. The invention exhibits merits against cancers such as significantly higher potency and effectiveness over a broader range of cancers. In formula (I), R a is a benzyl group with alkyl and/or alkoxy; R b is selected from H and alkyl groups; R f is an alkyl; and R 3 is selected from a substituted phenyl, a heterocyclic group, and wherein Rc is selected from a fused ring, fused rings, and any bivalent cyclic group.

  该发明提供了一种式(I)的化合物，其药物组成物，用于治疗癌症的药物制备方法，以及治疗癌症的方法。该发明展示了针对癌症的优点，如在更广泛的癌症范围内具有显着更高的效力和有效性。在式(I)中，R是含有烷基和/或烷氧基的苄基；R被选自H和烷基；Rf是烷基；而R3被选自取代苯基、杂环基，以及其中Rc被选自融合环、融合环和任何二价环状基团。
• US8802895B2
  申请人：——

  公开号：US8802895B2

  公开（公告）日：2014-08-12
• [EN] AMIDE DERIVATIVES OF BENZENE-SULFONANILIDE, PHARMACEUTICAL COMPOSITION THEREOF AND METHOD FOR CANCER TREATMENT USING THE SAME<br/>[FR] DÉRIVÉS AMIDE DE BENZÈNE-SULFONANILIDE, COMPOSITION PHARMACEUTIQUE LES CONTENANT ET MÉTHODE DE TRAITEMENT DU CANCER LES UTILISANT
  申请人：UNIV STATE CLEVELAND

  公开号：WO2012054417A1

  公开（公告）日：2012-04-26

  The invention provides a compound of formula (I), a pharmaceutical composition thereof, a method of preparing a medicament for the treatment of a cancer, and a method of treating cancers. The invention exhibits merits against cancers such as significantly higher potency and effectiveness over a broader range of cancers. In formula (I), Ra is a benzyl group with alkyl and/or alkoxy; Rb is selected from H and alkyl groups; Rf is an alkyl; and R3 is selected from a (Formula) substituted phenyl, a heterocyclic group, and, Formula, wherein Rc is selected from a fused ring, fused rings, and any bivalent cyclic group. Formula (I)
• From COX-2 inhibitor nimesulide to potent anti-cancer agent: Synthesis, in vitro, in vivo and pharmacokinetic evaluation
  作者：Bo Zhong、Xiaohan Cai、Snigdha Chennamaneni、Xin Yi、Lili Liu、John J. Pink、Afshin Dowlati、Yan Xu、Aimin Zhou、Bin Su

  DOI：10.1016/j.ejmech.2011.11.012

  日期：2012.1

  Cyclooxygenase-2 (COX-2) inhibitor nimesulide inhibits the proliferation of various types of cancer cells mainly via COX-2 independent mechanisms, which makes it a good lead compound for anti-cancer drug development. In the presented study, a series of new nimesulide analogs were synthesized based on the structure function analysis generated previously. Some of them displayed very potent anti-cancer activity with IC(50)s around 100 nM-200 nM to inhibit SKBR-3 breast cancer cell growth. CSUOH0901 (NSC751382) from the compound library also inhibits the growth of the 60 cancer cell lines used at National Cancer Institute Developmental therapeutics Program (NCIDTP) with IC(50)s around 100 nM-500 nM. Intraperitoneal injection with a dosage of 5 mg/kg/d of CSUOH0901 to nude mice suppresses HT29 colorectal xenograft growth. Pharmacokinetic studies demonstrate the good bioavailability of the compound. Published by Elsevier Masson SAS.