6-oxo-6,7,8,9,10,11-hexahydrocyclohepta[c]chromen-3-yl 4-methylbenzenesulfonate | 1538626-35-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环庚吡喃类
• 英文名称: 6-oxo-6,7,8,9,10,11-hexahydrocyclohepta[c]chromen-3-yl 4-methylbenzenesulfonate
• 英文别名: (6-oxo-8,9,10,11-tetrahydro-7H-cyclohepta[c]chromen-3-yl) 4-methylbenzenesulfonate
• CAS: 1538626-35-5
• 化学式: C₂₁H₂₀O₅S
• 分子量: 384.453
• InChiKey: BKGNSHSNDFIPBN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  78
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-氧代环庚烷甲酸乙酯 在 硫酸 、 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 6-oxo-6,7,8,9,10,11-hexahydrocyclohepta[c]chromen-3-yl 4-methylbenzenesulfonate
  参考文献：
  名称：

  Synthesis of tricyclic fused coumarin sulfonates and their inhibitory effects on LPS-induced nitric oxide and PGE2 productions in RAW 264.7 macrophages

  摘要：

  The regulations of NO and PGE(2) productions are research topics of interest in the field of antiinflammatory drug development. In the present study, a series of tricyclic fused coumarin sulfonate derivatives was synthesized and evaluated for their abilities to inhibit NO and PGE(2) productions in LPS-induced RAW 264.7 macrophages. Among all the target compounds, compound 1g possessing p-(trifluoromethyl) phenyl and fused cycloheptane moieties showed the highest inhibitory effects on NO and PGE2 productions. Compound 1g not only inhibited COX-2 activity but also reduced expressions of COX-2 and iNOS. Furthermore, ADME profiling showed that compounds 1g, 1j, 1m, and 1n are estimated to be orally bioavailable. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.12.018

文献信息

• Tricyclic coumarin sulphonate derivatives with alkaline phosphatase inhibitory effects: <i>in vitro</i> and docking studies
  作者：Jamshed Iqbal、Mohammed I. El-Gamal、Syeda Abida Ejaz、Joanna Lecka、Jean Sévigny、Chang-Hyun Oh

  DOI：10.1080/14756366.2018.1428193

  日期：2018.1.1

  tricyclic coumarin sulphonate 1a-za with known antiproliferative activity, was evaluated for AP inhibition against human tissue nonspecific alkaline phosphatase (h-TNAP) and human intestinal alkaline phosphatase (h-IAP). The methylbenzenesulphonate derivative 1f (IC50 = 0.38 ± 0.01 μM) was found to be the most active h-TNAP inhibitor. Another 4-fluorobenzenesulphonate derivative 1i (IC50 = 0.45 ± 0

  组织非特异性碱性磷酸酶（TNAP）是碱性磷酸酶的重要同工酶，在人体中起着不同的关键作用。最重要的是，它负责维持磷酸盐和无机焦磷酸盐的平衡比例，从而在骨骼形成和生长过程中调节细胞外基质钙化。TNAP水平升高与血管钙化和晚期肾脏疾病有关。因此，需要寻找强效​​和选择性的碱性磷酸酶（AP）抑制剂以治疗与AP过表达相关的疾病。在这里，一系列具有已知抗增殖活性的三环香豆素磺酸盐1a-za，评估AP对人组织非特异性碱性磷酸酶（h-TNAP）和人肠碱性磷酸酶（h-IAP）的抑制作用。发现甲基苯磺酸酯衍生物1f（IC50 = 0.38±0.01μM）是最具活性的h-TNAP抑制剂。发现另一种4-氟苯磺酸盐衍生物1i（IC50 = 0.45±0.02μM）是h-IAP的最强抑制剂。一些衍生物也被鉴定为AP的高选择性抑制剂。研究了详细的结构-活性关系（SAR），以鉴定负责有效抑制AP同工酶的官能团。该研究还受
• Synthesis, in vitro antiproliferative activity, and in silico studies of fused tricyclic coumarin sulfonate derivatives
  作者：Mohammed I. El-Gamal、Chang-Hyun Oh

  DOI：10.1016/j.ejmech.2014.06.064

  日期：2014.9

  A series of fused tricyclic coumarin sulfonate derivatives was synthesized. Their in vitro antiproliferative activities against a panel of 57 human cancer cell lines of nine different cancer types were tested at the NCI. Compounds 1e, 1f, 1h, 1i, and 1o showed the highest mean percentage of inhibition values over the 57 cell line panel at 10 μM, and they were further tested in 5-dose testing mode to determine their IC50 values. Compounds 1e, 1f, and 1o were more selective against leukemia and colon cancer subpanels, while compounds 1h and 1i showed broad-spectrum anticancer activities. Compounds 1e, 1f, 1h, 1i, and 1o demonstrated high selectivity towards cancer cell lines than RAW 264.7 macrophages. Compound 1h exerted lethal effect over NCI-H522 NSCLC, SK-MEL-5 melanoma, and A498 renal cancer cell lines with percentage of inhibition values of 114.10%, 103.23%, and 100.52% at 10 μM concentration, respectively. Moreover, the IC50 value of compound 1o against HT29 colon cancer cell line was 532 nM. Compounds 1e, 1f, 1h, 1i, and 1o were tested for inhibitory effect over cyclooxygenase-2 (COX-2) enzyme as a possible mechanism of action. Furthermore, in silico studies were conducted to check the compliance of those five compounds with Lipinski's rule of five, and hence estimate their oral bioavailability.
• Synthesis of tricyclic fused coumarin sulfonates and their inhibitory effects on LPS-induced nitric oxide and PGE2 productions in RAW 264.7 macrophages
  作者：Hyeon-Lok Jang、Mohammed I. El-Gamal、Hye-Eun Choi、Ho-Yeong Choi、Kyung-Tae Lee、Chang-Hyun Oh

  DOI：10.1016/j.bmcl.2013.12.018

  日期：2014.1

  The regulations of NO and PGE(2) productions are research topics of interest in the field of antiinflammatory drug development. In the present study, a series of tricyclic fused coumarin sulfonate derivatives was synthesized and evaluated for their abilities to inhibit NO and PGE(2) productions in LPS-induced RAW 264.7 macrophages. Among all the target compounds, compound 1g possessing p-(trifluoromethyl) phenyl and fused cycloheptane moieties showed the highest inhibitory effects on NO and PGE2 productions. Compound 1g not only inhibited COX-2 activity but also reduced expressions of COX-2 and iNOS. Furthermore, ADME profiling showed that compounds 1g, 1j, 1m, and 1n are estimated to be orally bioavailable. (C) 2013 Elsevier Ltd. All rights reserved.