4,4-dimethyl-6-<(E)-1-(4-carboxyphenyl)-1-propen-2-yl>-3,4-dihydro-2H-1-benzothiopyran | 91587-07-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 4,4-dimethyl-6-<(E)-1-(4-carboxyphenyl)-1-propen-2-yl>-3,4-dihydro-2H-1-benzothiopyran
• 英文别名: 4-[(E)-2-(4,4-dimethyl-6-thiochromanyl)-2-methylvinyl]benzoic acid；6-(1-(4-Carboxyphenyl)-1E-propen-2-yl)-3,4-dihydro-4,4-dimethyl-2H-1-benzothiopyran；4-[(E)-2-(4,4-dimethyl-2,3-dihydrothiochromen-6-yl)prop-1-enyl]benzoic acid
• CAS: 91587-07-4
• 化学式: C₂₁H₂₂O₂S
• 分子量: 338.47
• InChiKey: IHZBEOZNOCNBRM-WYMLVPIESA-N

物化性质

• 沸点：
  505.0±50.0 °C(Predicted)
• 密度：
  1.168±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  62.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4,4-dimethyl-6-<(E)-1-(4-carboxyphenyl)-1-propen-2-yl>-3,4-dihydro-2H-1-benzothiopyran 在 sodium chloride 、 间氯过氧苯甲酸 作用下， 以 氯仿 为溶剂， 生成 4-[(E)-2-(1,1-Dioxo-4,4-dimethyl-6-thiochromanyl)-2-methylvinyl]benzoic Acid
  参考文献：
  名称：

  Method for inhibiting the degradation of cartilage

  摘要：

  当给患有关节炎疾病的哺乳动物主体施用具有以下结构的某些羧酸（##STR1##）及其药用可接受的盐、某些酯和酰胺时，可用于抑制关节软骨的降解。X为O、S、SO、SO.sub.2、NH、NCH.sub.3或NCOCH.sub.3；n为零或一。

  公开号：

  US04808597A1
• 作为产物：
  描述：

  [(3-甲基丁-2-烯-1-基)硫代]苯 在 氢氧化钾 、 三氯化铝 、 15-冠醚-5 、 四氯化锡 、 sodium hydride 作用下， 以 四氢呋喃 、 二硫化碳 、 乙醇 、 二氯甲烷 为溶剂， 反应 40.25h， 生成 4,4-dimethyl-6-<(E)-1-(4-carboxyphenyl)-1-propen-2-yl>-3,4-dihydro-2H-1-benzothiopyran
  参考文献：
  名称：

  Conformationally restricted retinoids

  摘要：

  A series of conformationally restricted retinoids was synthesized and screened in two assays used to measure the ability of retinoids to control cell differentiation, namely, the reversal of keratinization in tracheal organ culture from vitamin A deficient hamsters and the inhibition of the induction of mouse epidermal ornithine decarboxylase by a tumor promoter. These compounds had bonds corresponding to selected bonds of the E-tetraene chain of retinoic acid (1) held in a planar cisoid conformation by inclusion in an aromatic ring. The meta-substituted analogue 3 of 4-[(E)-2-methyl-4-(2,6,6-trimethylcyclohexenyl)-1,3-butadienyl+ ++]benzoic acid (2) was far less active than 2 in both assays. In contrast, the vinyl homologue of 2 (4) and the 7,8-dihydro and 7,8-methano analogues (5 and 6) had activity comparable to that of 2. Analogues of 4-[(E)-2-(1,1,4,4-tetramethyl-1,2,3,4-tetrahydro-6-naphthyl)propenyl] benzoic acid (7) were also screened. Replacement of the tetrahydronaphthalene ring of 7 by a benzonorbornenyl group (9) significantly reduced activity, as did removal of the vinylic methyl group from 9 (10). Replacement of the propenyl group of 9 by a cyclopropane ring (12) also reduced activity. Replacement of the tetrahydronaphthalene ring of 7 by 4,4-dimethyl-3,4-dihydro-2H-1-benzopyran and -benzothiopyran rings (13 and 14) also decreased activity. Inclusion of the 7,9 double bond system of 1 in an aromatic ring (15 and 16) reduced activity, whereas inclusion of the 5,7 double bond system in an aromatic ring enhanced activity (7 and 19). Inclusion of the 11,13 and 9,11,13 double bond systems in aromatic rings (2 and 18) also reduced activity below that of 1. Retinoic acid, 7, 13, 14, and 19 inhibited papilloma tumor formation in mice. Toxicity testing indicated that 7 was more toxic than 1, 13, 14, and 19, 19 was more toxic than 1, and 13 and 14 were less toxic than 1.

  DOI：

  10.1021/jm00377a022

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 M. Doris

  公开号：US20060252817A1

  公开（公告）日：2006-11-09

  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) hemophilia, (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.

  本发明考虑了通过施用柔性杂芳香类化合物来治疗、减轻、抑制或预防多种疾病的方法。可以从本文所述的柔性杂芳香类化合物治疗中获益的疾病或病症包括：(1) 癌症和其他涉及异常分化的疾病；(2) 糖尿病；(3) 血友病；(4) 肝病、(5) 涉及人类醛脱氢酶 2 的疾病；(6) 多囊肾；(7) 溶酶体贮存疾病；(8) 高胆固醇；(9) 肥胖症；(10) 高甘油三酯；(11) 糖蛋白代谢疾病；以及 (12) 涉及血管生成异常的疾病。
• HOFFMAN, WILLIAM W.;KRASKA, ALLEN R.
  作者：HOFFMAN, WILLIAM W.、KRASKA, ALLEN R.

  DOI：——

  日期：——
• Carboxylic acid derivatives useful for inhibiting the degradation of cartilage
  申请人：PFIZER INC.

  公开号：EP0130795B1

  公开（公告）日：1988-11-23