3-(Benzenesulfonyl)-4-chlorochromen-2-one | 193684-77-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 3-(Benzenesulfonyl)-4-chlorochromen-2-one
• CAS: 193684-77-4
• 化学式: C₁₅H₉ClO₄S
• 分子量: 320.753
• InChiKey: HLICLMGMEMTMCO-UHFFFAOYSA-N

物化性质

• 沸点：
  532.5±50.0 °C(Predicted)
• 密度：
  1.54±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  68.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(Benzenesulfonyl)-4-chlorochromen-2-one 在 氯化铵 、 三氟乙酸 、 锌 作用下， 以 四氢呋喃 为溶剂， 生成 (S)-5-Oxo-1-(2-oxo-2H-chromen-4-yl)-pyrrolidine-2-carboxylic acid
  参考文献：
  名称：

  New Crystalline N-(Coumarin-4-yl)-L-pyroglutamic Acid. The First Synthesis and Application to 1H NMR Optical Purity Determination of Alcohols and Amines

  摘要：

  Condensation of 3-phenylsulfonyl-4-chlorocoumarin with tert-butyl L-pyroglutamate potassium salt followed by desulfonylation and ester-cleavage yielded the novel crystalline N-(coumarin-4-yl)-L-pyro-glutamic acid[CPYR0-0H], which being evidenced to be a versatile and reliable H-1 nmr optical purity determination agent for chiral alcohols and amines.

  DOI：

  10.3987/com-97-7775
• 作为产物：
  描述：

  3-(2-Acetoxy-phenyl)-2-benzenesulfonyl-3-oxo-propionic acid methyl ester 在 盐酸 、 lithium hydroxide 、 三氯氧磷 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 3-(Benzenesulfonyl)-4-chlorochromen-2-one
  参考文献：
  名称：

  New Crystalline N-(Coumarin-4-yl)-L-pyroglutamic Acid. The First Synthesis and Application to 1H NMR Optical Purity Determination of Alcohols and Amines

  摘要：

  Condensation of 3-phenylsulfonyl-4-chlorocoumarin with tert-butyl L-pyroglutamate potassium salt followed by desulfonylation and ester-cleavage yielded the novel crystalline N-(coumarin-4-yl)-L-pyro-glutamic acid[CPYR0-0H], which being evidenced to be a versatile and reliable H-1 nmr optical purity determination agent for chiral alcohols and amines.

  DOI：

  10.3987/com-97-7775

文献信息

• Antiproliferative Effect of <i>N</i>-Heterocyclo-Coumarin Derivatives against Multidrug-Resistant Cells
  作者：Koji Wada、Masuo Goto、Kuo-Hsiung Lee、Hiroshi Yamashita

  DOI：10.1248/cpb.c22-00585

  日期：2023.1.1

  Chemotherapy refers principally to the use of small molecules to treat cancer, and natural product derivatives have been main sources of clinically using anticancer drugs. While the coumarin skeleton does not inhibit cell growth, its derivatives are often active, and numerous coumarins have been examined for antiproliferative activity against human cancer cell lines. In this study, 16 novel coumarin derivatives (1, 1a–5a, 1b, 2b, 6b, 7b, 8–13) with attached N-heterocycles, including aminopyrrolidine, aminopiperidine, aminoazepane, and indoline, were prepared and ultimately esterified or amidated with alcohols or amines, respectively. All synthesized N-heterocycles containing coumarin derivatives with alcohols, amines, and carboxylic acids were assessed for antiproliferative activity against several human cancer cell lines, containing triple-negative breast cancer (TNBC) as well as a P-glycoprotein (P-gp) overexpressing multidrug-resistant (MDR) KB subline KB-VIN. Five coumarin derivatives (3a–5a, 12, 13) showed no effect (IC50 >40 µM) against all tested cell lines. In contrast, derivative 1a showed broad-spectrum activity against four cell lines, while 1b and 10 were nearly twice as selective for KB-VIN cells as the parent KB. The coumarin derivatives 1a, 1b, and 10 were optimal for antiproliferative activity in this study and could provide a new avenue for overcoming MDR tumors. Derivatives 1a, 1b, and 10 showed MDR cell-selective antiproliferative activity, indicating that N-heterocycle-coumarins exert previously unexplored bioactivity with selective action on MDR cancer cells.

  化疗主要指使用小分子治疗癌症，天然产物衍生物一直是临床上使用抗癌药物的主要来源。虽然香豆素骨架不能抑制细胞生长，但其衍生物通常具有活性，许多香豆素已被证实对人类癌细胞系具有抗增殖活性。在这项研究中，制备了16种新型香豆素衍生物（1、1a-5a、1b、2b、6b、7b、8-13），这些衍生物带有N杂环，包括氨基吡咯烷、氨基哌啶、氨基氮杂环庚烷和吲哚啉，并最终分别与醇或胺酯化或酰胺化。对所有合成的含香豆素衍生物的N杂环与醇、胺和羧酸的混合物进行了评估，以确定其对几种人类癌细胞系的抗增殖活性，包括三阴性乳腺癌（TNBC）以及P-糖蛋白（P-gp）过度表达的多药耐药（MDR）KB子系KB-VIN。五种香豆素衍生物（3a-5a、12、13）对所有测试的细胞系均无影响（IC50>40μM）。相比之下，衍生物1a对四种细胞系具有广谱活性，而1b和10对KB-VIN细胞的选择性几乎是母体KB的两倍。在这