SHetA2 | 361483-66-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 硫铬烷
• 英文名称: SHetA2
• 英文别名: 1-(4-nitrophenyl)-3-(2,2,4,4-tetramethyl-3H-thiochromen-6-yl)thiourea
• CAS: 361483-66-1
• 化学式: C₂₀H₂₃N₃O₂S₂
• 分子量: 401.554
• InChiKey: FWWKIYPMUZVMQG-UHFFFAOYSA-N

物化性质

• 熔点：
  153-155 °C(Solv: chloroform (67-66-3); pentane (109-66-0))
• 沸点：
  522.6±60.0 °C(Predicted)
• 密度：
  1.284±0.06 g/cm3(Predicted)
• 溶解度：
  DMSO: 2mg/mL, clear

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  127
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2,2,4,4-tetramethylthiochroman 在 硝酸 、 乙酸酐 、 铁粉 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 37.5h， 生成 SHetA2
  参考文献：
  名称：

  Synthesis of Flexible Sulfur-Containing Heteroarotinoids That Induce Apoptosis and Reactive Oxygen Species with Discrimination between Malignant and Benign Cells

  摘要：

  Regulation of growth, differentiation, and apoptosis by synthetic retinoids can occur through mechanisms that are dependent and independent of their ability to bind and activate nuclear retinoic acid receptors. The objective of this study was to determine if increasing flexibility of the heteroarotinoid structure would affect the specificity of the synthetic retinoids for the receptors and for their regulation of cancerous and nonmalignant cells. Methods were developed to produce the first examples of heteroarotinoids 15a-15h, which contain urea and/or thiourea linking groups between two aryl rings. Substituents at the para position of the single phenyl ring were either an ester, a nitro group, or a sulfonamide group. Ovarian cancer cell lines Caov-3, OVCAR-3, SK-OV-3, UCI-101, and 222 were utilized, and the inhibitory prowess of the heteroarotinoids was referenced to that of 4-HPR (25). Similar to 4-HPR (25), the heteroarotinoids inhibited growth of all cell lines at micromolar concentrations. Although the heteroarotinoids did not activate retinoic acid receptors, the agents induced potent growth inhibition against the cancer cells with weak activity against normal and benign cells. The growth inhibition was associated with cell loss and induction of reactive oxygen species.

  DOI：

  10.1021/jm030346v

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。
• TREATMENT AND INHIBITION OF DISEASE CONDITIONS USING FLEXIBLE HETEROAROTINOIDS
  申请人：Benbrook Doris M.

  公开号：US20100105757A1

  公开（公告）日：2010-04-29

  The present invention contemplates methods of treating, reducing, inhibiting or preventing several diseases by the administration of flexible heteroarotinoids. Among the diseases or conditions which can benefit from treatment with flexible heteroarotinoids as described herein are, (1) cancers and other diseases that involve abnormal differentiation, (2) diabetes, (3) hemophelia, (4) liver disease, (5) diseases involving human aldehyde dehydrogenase 2, (6) polycystic kidney disease, (7) lysosomal storage diseases, (8) high cholesterol, (9) obesity, (10) high triglycerides, (11) glycoprotein metabolism diseases, and (12) diseases involving abnormal angiogenesis.
• US7612107B2
  申请人：——

  公开号：US7612107B2

  公开（公告）日：2009-11-03