3-(1,3-dioxolan-2-yl)benzoic acid | 773101-97-6

• 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: 3-(1,3-dioxolan-2-yl)benzoic acid
• CAS: 773101-97-6
• 化学式: C₁₀H₁₀O₄
• mdl: MFCD06209118
• 分子量: 194.187
• InChiKey: CKOQSKSHQSFICH-UHFFFAOYSA-N

物化性质

• 熔点：
  115.1-115.2 °C(Solv: toluene (108-88-3))
• 沸点：
  367.9±37.0 °C(Predicted)
• 密度：
  1.316±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(1,3-dioxolan-2-yl)benzoic acid 在 吡啶 、 sodium hydroxide 、 正丁基锂 、 氯化亚砜 、 高氯酸 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 99.0h， 生成 trans-3-[3-(1-benzenesulfonyl-1H-indole-2-carbonyl)phenyl]-N-(tetrahydropyran-2-yloxy)acrylamide
  参考文献：
  名称：

  2-Aroylindoles and 2-Aroylbenzofurans with N-Hydroxyacrylamide Substructures as a Novel Series of Rationally Designed Histone Deacetylase Inhibitors

  摘要：

  Histone deacetylase (HDAC) inhibitors are considered to be drugs for targeted cancer therapy and second-generation HDIs are currently being tested in clinical trials. Here, we report on the synthesis and biological evaluation of a novel HDAC inhibitor scaffold with the hydroxamate Zn2+ complexing headgroup, selected from the 2-aroylindol motif. Inhibition of nuclear extract HDAC and recombinant HDAC I as well as induction of histone H3K(9+14) hyperacetylation mediated by E-N-hydroxy-(2-aroylindole)acrylamides or E-Nhydroxy-(2-aroylbenzofuran)acrylamides were studied. Moreover, the cytotoxic activity, the effects on the cell cycle, and historic H3S(10) phosphorylation of selected compounds were determined. By use of a panel of 24 different human tumor cell lines, mean IC50 values of the most potent analogues 6c and 7b were 0.75 and 0.65 mu M, respectively. The novel compounds were shown to be no substrates of the P-glycoprotein drug transporter. Comparable to N-1-hydroxy-N-8-phenyloctanediamide "2 (SAHA)", cells in the S phase of the cell cycle are depleted, with partial arrest in G1 and G2/M and finally induction of massive apoptosis.

  DOI：

  10.1021/jm0703136
• 作为产物：
  描述：

  3-羧基苯甲醛 、 乙二醇 在 aluminum oxide 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以69%的产率得到3-(1,3-dioxolan-2-yl)benzoic acid
  参考文献：
  名称：

  2-Aroylindoles and 2-Aroylbenzofurans with N-Hydroxyacrylamide Substructures as a Novel Series of Rationally Designed Histone Deacetylase Inhibitors

  摘要：

  Histone deacetylase (HDAC) inhibitors are considered to be drugs for targeted cancer therapy and second-generation HDIs are currently being tested in clinical trials. Here, we report on the synthesis and biological evaluation of a novel HDAC inhibitor scaffold with the hydroxamate Zn2+ complexing headgroup, selected from the 2-aroylindol motif. Inhibition of nuclear extract HDAC and recombinant HDAC I as well as induction of histone H3K(9+14) hyperacetylation mediated by E-N-hydroxy-(2-aroylindole)acrylamides or E-Nhydroxy-(2-aroylbenzofuran)acrylamides were studied. Moreover, the cytotoxic activity, the effects on the cell cycle, and historic H3S(10) phosphorylation of selected compounds were determined. By use of a panel of 24 different human tumor cell lines, mean IC50 values of the most potent analogues 6c and 7b were 0.75 and 0.65 mu M, respectively. The novel compounds were shown to be no substrates of the P-glycoprotein drug transporter. Comparable to N-1-hydroxy-N-8-phenyloctanediamide "2 (SAHA)", cells in the S phase of the cell cycle are depleted, with partial arrest in G1 and G2/M and finally induction of massive apoptosis.

  DOI：

  10.1021/jm0703136

文献信息

• [EN] COMPOSITIONS AND METHODS FOR IMMUNE MODULATION AND TREATMENT OF CANCER<br/>[FR] COMPOSITIONS ET MÉTHODES DE MODULATION IMMUNITAIRE ET DE TRAITEMENT DU CANCER
  申请人：UNIV MICHIGAN STATE

  公开号：WO2020150668A1

  公开（公告）日：2020-07-23

  The disclosure relates to rexinoids, including compounds of the Formula (I) and (II) or a pharmaceutically acceptable salt, polymorph, prodrug, solvate or clathrate thereof. These rexinoids are useful for increasing PD-L1 in vivo, for treatment of cancer, and for inhibiting the onset of cancer.

  该披露涉及雷克西酮，包括式(I)和(II)的化合物或其药用可接受的盐、多型体、前药、溶剂合物或包合物。这些雷克西酮对于体内增加PD-L1，在癌症治疗中以及抑制癌症发生方面是有用的。
• Cinnamoyl compound and use of the same
  申请人：Tomigahara Yoshitaka

  公开号：US20060211680A1

  公开（公告）日：2006-09-21

  The present invention relates to a cinnamoyl compound represented by the formula (I):

  本发明涉及一种由式(I)表示的肉桂酰化合物。
• Novel therapeutic compounds
  申请人：Breinlinger Eric C.

  公开号：US20090069288A1

  公开（公告）日：2009-03-12

  Disclosed herein are novel compounds of Formula (I), wherein the variables are defined as herein. The compounds of Formula (I) are useful as kinase inhibitors and as such would be useful in treating certain conditions and diseases, especially inflammatory conditions and diseases as well as proliferative disorders such as cancer.

  本文公开了公式（I）的新化合物，其中变量如本文所定义。公式（I）的化合物可用作激酶抑制剂，因此可用于治疗某些疾病和病症，特别是炎症性疾病和疾病以及增生性疾病，如癌症。
• CINNAMOYL COMPOUND AND USE OF THE SAME
  申请人：Sumitomo Chemical Company, Limited

  公开号：EP1671961A1

  公开（公告）日：2006-06-21

  The present invention relates to a cinnamoyl compound represented by the formula (I):

  本发明涉及一种由式 (I) 代表的肉桂酰化合物：
• EP1671948
  申请人：——

  公开号：——

  公开（公告）日：——