N-[3,4-dihydro-4-(acetoxymethyl)-2,2,4-trimethyl-2H-1-benzothiopyran-6-yl]-N'-(4-nitrophenyl)thiourea | 1270009-64-7

• 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-[3,4-dihydro-4-(acetoxymethyl)-2,2,4-trimethyl-2H-1-benzothiopyran-6-yl]-N'-(4-nitrophenyl)thiourea
• 英文别名: [2,2,4-trimethyl-6-[(4-nitrophenyl)carbamothioylamino]-3H-thiochromen-4-yl]methyl acetate
• CAS: 1270009-64-7
• 化学式: C₂₂H₂₅N₃O₄S₂
• 分子量: 459.59
• InChiKey: WWYVISWEWSZKBF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  154
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2,2-二甲基-2,3-二氢-1-苯并噻喃-4-酮 在 吡啶 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 硫酸 、 水 、 硝酸 、 乙酸酐 、 铁粉 、 sodium hydride 、 溶剂黄146 、 zinc(II) iodide 、 三氯氧磷 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 64.75h， 生成 N-[3,4-dihydro-4-(acetoxymethyl)-2,2,4-trimethyl-2H-1-benzothiopyran-6-yl]-N'-(4-nitrophenyl)thiourea
  参考文献：
  名称：

  Synthesis of N-[3,4-Dihydro-4-(acetoxymethyl)-2,2,4-trimethyl-2H-1-benzothiopyran-6-yl]-N′-(4-nitrophenyl)thiourea and N-[3,4-dihydro-4-(hydroxymethyl)-2,2,4-trimethyl-2H-1-benzothiopyran-6-yl]-N′-(4-nitrophenyl)thiourea, a Major Metabolite of N-(3,4-Dihydro-2,2,4,4-tetramethyl-2H-1-benzothiopyran-6-YL)-N′-(4-nitrophenyl)thiourea

  摘要：

  The compound N-(3,4-dihydro-2,2,4,4-tetramethyl-2H-1-benzothiopyran-6-yl)-N'-(4-nitrophenyl)thiourea [NSC 726189] has exhibited strong anticancer activity in several assays and cell lines and is under consideration for clinical trials for the possible treatment of kidney cancer. Since the heterocycle has not shown any significant toxicity in animal studies, it is conceivable that a metabolite could be the active agent. In a previous study, major metabolites were tentatively identified via analyses of materials extracted from rat and human liver microsomes, as well as extracts from rat urine, by the use of HPLC-UV and MS/MS. However, no metabolite has been obtained in pure form. This article outlines a de novo synthesis of a primary metabolite, namely N-[3,4-dihydro-4-(hydroxymethyl)-2,2,4-trimethyl-2H-1-benzothiopyran-6-yl]-N'-(4-nitrophenyl)thiourea. A prodrug of the metabolite was also prepared, namely N-[3,4-dihydro-4-(acetoxymethyl)-2,2,4-trimethyl-2H-1-benzothiopyran-6-yl]-N'-(4-nitrophenyl)thio-urea. GRAPHICAL ABSTRACT[image omitted].

  DOI：

  10.1080/10426507.2010.534521

文献信息

• CHROMAN-SUBSTITUTED, TETRAHYDROQUINOLINE-SUBSTITUTED AND THIOCHROMAN-SUBSTITUTED HETEROAROTINOIDS AS ANTI-CANCER AGENTS
  申请人：THE BOARD OF REGENTS FOR OKLAHOMA STATE UNIVERSITY

  公开号：US20200062711A1

  公开（公告）日：2020-02-27

  Chemical compounds that inhibit cancer cell growth are provided. The compounds are heteroarotinoids and derivatives thereof with oxygen, nitrogen or sulfur in chroman systems, tetrahydroquinoline systems, and tetrahydrothiochroman systems.

  提供了抑制癌细胞生长的化合物。这些化合物是杂环维生素A类化合物及其衍生物，其在色酮系统、四氢喹啉系统和四氢硫色酮系统中含有氧、氮或硫。
• Chroman-substituted, tetrahydroquinoline-substituted and thiochroman-substituted heteroarotinoids as anti-cancer agents
  申请人：THE BOARD OF REGENTS FOR OKLAHOMA STATE UNIVERSITY

  公开号：US10947198B2

  公开（公告）日：2021-03-16

  Chemical compounds that inhibit cancer cell growth are provided. The compounds are heteroarotinoids and derivatives thereof with oxygen, nitrogen or sulfur in chroman systems, tetrahydroquinoline systems, and tetrahydrothiochroman systems.

  提供了抑制癌细胞生长的化学物质。这些化合物是杂芳基类化合物及其衍生物，在铬烷体系、四氢喹啉体系和四氢硫铬烷体系中含有氧、氮或硫。