4-methyl-piperazine-1-carbothioic acid benzoylamide | 33860-29-6

• 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: 4-methyl-piperazine-1-carbothioic acid benzoylamide
• 英文别名: N-Benzoyl-4-methyl-1-piperazinthiocarboxamid；N-(4-methylpiperazine-1-carbothioyl)benzamide
• CAS: 33860-29-6
• 化学式: C₁₃H₁₇N₃OS
• mdl: MFCD00761441
• 分子量: 263.363
• InChiKey: VMGFUNOZLVTEPX-UHFFFAOYSA-N

物化性质

• 密度：
  1.219±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  67.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-methyl-piperazine-1-carbothioic acid benzoylamide 、 2-(chloromethyl)-3-(4-chlorophenyl)quinazolin-4(3H)-one 在 三乙胺 作用下， 以 乙腈 为溶剂， 以55%的产率得到3-(4-chlorophenyl)-2-(2-(4-methylpiperazin-1-yl)-5-phenylthiazol-4-yl)quinazolin-4(3H)-one
  参考文献：
  名称：

  Synthesis and screening of 2-(2-(4-substituted piperazine-1-yl)-5-phenylthiazol-4-yl)-3-aryl quinazolinone derivatives as anticancer agents

  摘要：

  Synthesis of novel quinazolinone derivatives was performed from the reaction of N-benzoyl substituted piperazine-1-carbothioamide with 2-chloromethyl quinazolinone derivatives and screened for their in vitro cytotoxic activity by MTT assay. The cell lines used were NCI (human lung cancer cell), MCF 7 (Breast cancer cell), and HEK 293 (Normal epidermal kidney cell). Result of screening on cell line showed moderate to good anticancer activity for all the compounds. Compound 3d (IC50 = 1.1 +/- A 0.03 mu M) was found to be the most active compared to standard methotrexate (IC50 = 2.20 +/- A 0.18 mu M) and 5-florouracil (IC50 = 2.30 +/- A 0.49 mu M). Structure activity relationship of synthesized analogs suggested that the presence of NH linker with aryl moiety at the third position of quinazolinone ring was important for potent anticancer activity. Electron donating group on phenyl ring at the third position of quinazolinone ring gave better anticancer activity then unsubstituted phenyl and electron withdrawing group. Activity by substituted piperazine at 2nd position of thiazole linked with quinazolinone scaffold gave better activity in the order of H > CH3 > CO-C6H5. Our findings may impart new direction to medicinal chemists and biochemists for further investigations of quinazolinone-thiazole containing anticancer agents.

  DOI：

  10.1007/s00044-012-0260-2
• 作为产物：
  描述：

  N-甲基哌嗪 、 苯甲酰基异硫氰酸酯 以 乙酸乙酯 为溶剂， 生成 4-methyl-piperazine-1-carbothioic acid benzoylamide
  参考文献：
  名称：

  咪唑并[1,2- a ]吡啶与噻唑/噻吩基团通过酮间隔基连接作为潜在的细胞毒剂和NF-κB抑制剂

  摘要：

  合成了一系列新的通过酮间隔基与噻唑/噻吩基团连接的咪唑并[1,2- a ]吡啶，并使用MTT法测试了它们对三种人类癌细胞系（包括A549，HeLa和U87-MG）的细胞毒性潜力。化合物A2，A3，A4，C1和C2对所有三种细胞系均显示出细胞毒性。化合物A4对A549和HeLa细胞的选择性指数与阿霉素相当。在合成的化合物中，B5表现出对NF-κB活性的最大抑制作用，这是通过NF-κB报告基因分析确定的（IC 50 = 6.5±0.6 µM）。用埃洛替尼和吉非替尼以及化合物A4和B5处理NCI-H23细胞（EGFR过表达，KRAS G12V突变体）表明联合治疗具有协同作用和加成作用。

  DOI：

  10.1016/j.bmcl.2017.10.060

文献信息

• GLYCOSAMINOGLYCAN INHIBITORS
  申请人：Crawford Brett E.

  公开号：US20120295890A1

  公开（公告）日：2012-11-22

  Provided herein are chondroitin sulfate inhibitors, including modulators of glycosylation, and/or sulfation of galactose or N-acetyl galactosamine glycosaminoglycans.
• [EN] NOVEL THIOUREA OR UREA DERIVATIVE, PREPARATION METHOD THEREOF, AND PHARMACEUTICAL COMPOSITION FOR PREVENTING OR TREATING AIDS, CONTAINING SAME AS ACTIVE INGREDIENT<br/>[FR] NOUVELLE THIO-URÉE OU NOUVEAU DÉRIVÉ D'URÉE, PROCÉDÉ PERMETTANT LEUR PRÉPARATION, ET COMPOSITION PHARMACEUTIQUE DESTINÉE À PRÉVENIR OU À TRAITER LE SIDA, LES CONTENANT EN TANT QUE PRINCIPE ACTIF
  申请人：AVIXGEN INC

  公开号：WO2011159137A2

  公开（公告）日：2011-12-22

  본 발명은 신규한 티오우레아 또는 우레아 유도체, 이의 제조방법 및 이를 유효성분으로 함유하는 AIDS 예방 또는 치료용 약학 조성물에 관한 것이다. 본 발명에 따른 티오우레아 또는 우레아 유도체는 HIV 바이러스 발현을 억제함으로써 HIV 저해 활성이 우수하여 AIDS 예방 또는 치료에 유용하게 사용될 수 있다.