4-((2-(benzo[d][1,3]dioxol-5-ylmethyl)thiazol-4-yl)methoxy)-2-hydroxybenzaldehyde | 1206790-20-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 4-((2-(benzo[d][1,3]dioxol-5-ylmethyl)thiazol-4-yl)methoxy)-2-hydroxybenzaldehyde
• 英文别名: 4-((2-((benzo [d][1,3]dioxolan-5-yl)methyl)thiazol-4-yl)methoxy)-2-hydroxybenzaldehyde；2-hydroxy-4-{[2-(3,4-dioxomethylenebenzyl)methyl]thiazol-4-ylmethoxy}benzaldehyde；4-[[2-(1,3-Benzodioxol-5-ylmethyl)-1,3-thiazol-4-yl]methoxy]-2-hydroxybenzaldehyde；4-[[2-(1,3-benzodioxol-5-ylmethyl)-1,3-thiazol-4-yl]methoxy]-2-hydroxybenzaldehyde
• CAS: 1206790-20-6
• 化学式: C₁₉H₁₅NO₅S
• 分子量: 369.398
• InChiKey: DAHCIFWLPRRFNE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  106
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-((2-(benzo[d][1,3]dioxol-5-ylmethyl)thiazol-4-yl)methoxy)-2-hydroxybenzaldehyde 、 N-(6-((diethylamino)methyl)benzo[d]thiazol-2-yl)hydrazinecarboxamide 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以79%的产率得到(E)-N-(6-((diethylamino)methyl)benzo[d]thiazol-2-yl)-2-(4-((2-(benzo[d][1,3]dioxol-5-ylmethyl)thiazol-4-yl)methoxy)-2-hydroxybenzylidene)hydrazinecarboxamide
  参考文献：
  名称：

  Design, synthesis, and structure–activity relationships of novel benzothiazole derivatives bearing the ortho-hydroxy N-carbamoylhydrazone moiety as potent antitumor agents

  摘要：

  A series of novel benzothiazole derivatives bearing the ortho-hydroxy N-carbamoylhydrazone moiety were designed and synthesized and their cytotoxic activities against five cancer cell lines (NCI-H226, SK-N-SH, HT29, MKN45, and MDA-MB-231) were screened in vitro. Most of them showed moderate to excellent activity against all the tested cell lines. Among them, compounds 15g (procaspase-3 EC50 = 1.42 mu M) and 16b (procaspase-3 EC50 = 0.25 mu M) exhibited excellent antitumor activity with IC50 values ranging from 0.14 mu M to 0.98 mu M against all cancer cell lines, which were 1.8-8.7 times more active than the first procaspase activating compound (PAC-1) (procaspase-3 EC50 = 4.08 mu M). The structure activity relationship (SAR) analyses indicated that the introduction of a lipophilic group (a benzyloxy or heteroaryloxy group) at the 4-position of the 2-hydroxy phenyl ring was beneficial to antitumor activity, and the presence of substituents containing nitrogen that are positively charged at physiological pH could also improve antitumor activity. It was also confirmed that the steric effect of the 4-position substituent of the benzyloxy group had a significant influence on cytotoxic activity. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.08.058
• 作为产物：
  描述：

  1,3-苯并二氧杂环戊烯-5-乙腈 在 sodium hydrogen sulfide 、 magnesium(II) chloride hexahydrate 、 碳酸氢钠 、 potassium iodide 作用下， 以 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 21.0h， 生成 4-((2-(benzo[d][1,3]dioxol-5-ylmethyl)thiazol-4-yl)methoxy)-2-hydroxybenzaldehyde
  参考文献：
  名称：

  带有苯基部分的半脲衍生物：合成，抗癌活性，细胞周期，细胞凋亡诱导和代谢稳定性研究。

  摘要：

  合成了一系列带有苯基部分的半脲衍生物，并评估了其在四种人类癌细胞系（人类结肠癌（HT29），人类神经母细胞瘤（SK-N-SH），人类乳腺癌（MDA-MB）中的体外抗癌活性-231）和人胃癌（MKN45））。生物学评估导致鉴定出11q和11s，它们对被测癌细胞具有优异的抗癌活性，IC50值分别为0.32至1.57 µM，而对正常细胞（人脐静脉内皮细胞（HUVEC））的细胞毒性较弱）。流式细胞仪检测细胞周期和细胞凋亡表明11q和11s导致Sub-G1细胞周期停滞，并通过剂量依赖性方式诱导细胞凋亡来抑制癌细胞的增殖。进一步的酶促测定表明11q和11s可以将procaspase-3显着激活为caspase-3。代谢稳定性研究表明，11q和11s在人和大鼠肝微粒体中显示出适度的体外稳定性。鉴于11q和11s具有良好的药理活性，已成为进一步发展癌症治疗的有价值的先导。

  DOI：

  10.1248/cpb.c18-00738

文献信息

• 缩氨基脲衍生物及其用途
  申请人：沈阳药科大学

  公开号：CN104230845B

  公开（公告）日：2017-01-25

  本发明属于医药技术领域，涉及通式Ⅰ所示的缩氨基脲衍生物，其几何异构体、及其药学上可接受的盐、溶剂化物或前药，其中取代基M、R1、R2、R、n具有在说明书中给出的定义。本发明还涉及制备式Ⅰ化合物的方法、含有上述化合物的药用组合物以及上述化合物及药用组合物用于制备治疗和/或预防癌症和其它增生性疾病的药物中的用途。
• SUBSTITUTED HYDRAZIDE COMPOUNDS AND USE THEREOF
  申请人：Shi Xiulan

  公开号：US20120142921A1

  公开（公告）日：2012-06-07

  The invention relates to substituted hydrazide compounds as shown by general formula I, including geometrical isomers, pharmaceutically acceptable salts, hydrates, solvates or prodrugs thereof, and use of the same, wherein the substitutents Ar and R have the same meanings as given in the Description. The invention further relates to the use of compounds of general formula I in the preparation of medicament for the treatment and/or prevention of cancer and other proliferative diseases.

  本发明涉及通式I所示的取代肼化合物，包括几何异构体、药学上可接受的盐、水合物、溶剂合物或前药，以及其使用，其中取代基Ar和R的含义与说明中给出的相同。本发明还涉及通式I化合物在制备用于治疗和/或预防癌症和其他增殖性疾病的药物中的使用。
• EP2468730
  申请人：——

  公开号：——

  公开（公告）日：——
• [EN] OXADIAZOLE-BASED PIPERAZINE DERIVATIVES AND APPLICATIONS THEREOF<br/>[FR] DÉRIVÉS DE PIPÉRAZINE À BASE D'OXADIAZOLE ET APPLICATIONS ASSOCIÉES
  申请人：UNIV SHENYANG PHARMACEUTICAL

  公开号：WO2011124087A1

  公开（公告）日：2011-10-13

  Disclosed are acethydrazide derivatives containing oxadiazole-based piperazine represented by the general formula I, geometric isomers thereof as well as pharmaceutically acceptable salts, hydrates or solvates thereof, which belong to the technical field of medicines. In formula I, substituent groups Ar1 and R1 have definitions given in the description. Methods for preparing the compounds of formula I, medicinal compositions containing the compounds as well as applications of the compounds for preparing medicines for treating and/or preventing cancers and other hyperplastic diseases are also disclosed.
• Semicarbazone Derivatives Bearing Phenyl Moiety: Synthesis, Anticancer Activity, Cell Cycle, Apoptosis-Inducing and Metabolic Stability Study
  作者：Junjie Ma、Xin Ni、Yali Gao、Kun Huang、Yu Wang、Jiaan Liu、Guowei Gong

  DOI：10.1248/cpb.c18-00738

  日期：2019.4.1

  of semicarbazone derivatives bearing phenyl moiety were synthesized and evaluated for the vitro anticancer activities in four human cancer cell lines (human colon cancer (HT29), human neuro-blastoma (SK-N-SH), human breast cancer (MDA-MB-231), and human gastric cancer (MKN45)). Biological evaluation led to the identification of 11q and 11s, which showed excellent anticancer activities against tested

  合成了一系列带有苯基部分的半脲衍生物，并评估了其在四种人类癌细胞系（人类结肠癌（HT29），人类神经母细胞瘤（SK-N-SH），人类乳腺癌（MDA-MB）中的体外抗癌活性-231）和人胃癌（MKN45））。生物学评估导致鉴定出11q和11s，它们对被测癌细胞具有优异的抗癌活性，IC50值分别为0.32至1.57 µM，而对正常细胞（人脐静脉内皮细胞（HUVEC））的细胞毒性较弱）。流式细胞仪检测细胞周期和细胞凋亡表明11q和11s导致Sub-G1细胞周期停滞，并通过剂量依赖性方式诱导细胞凋亡来抑制癌细胞的增殖。进一步的酶促测定表明11q和11s可以将procaspase-3显着激活为caspase-3。代谢稳定性研究表明，11q和11s在人和大鼠肝微粒体中显示出适度的体外稳定性。鉴于11q和11s具有良好的药理活性，已成为进一步发展癌症治疗的有价值的先导。