14-Sulfido-14-[1-[2-[(14-sulfido-13,15-dioxa-2-thia-14-phosphoniapentacyclo[14.8.0.03,12.04,9.019,24]tetracosa-1(16),3(12),4,6,8,10,17,19,21,23-decaen-14-yl)oxy]naphthalen-1-yl]sulfanylnaphthalen-2-yl]oxy-13,15-dioxa-2-thia-14-phosphoniapentacyclo[14.8.0.03,12.04,9.019,24]tetracosa-1(16),3(12),4,6,8,10,17,19,21,23-decaene | 1034498-38-8

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 14-Sulfido-14-[1-[2-[(14-sulfido-13,15-dioxa-2-thia-14-phosphoniapentacyclo[14.8.0.03,12.04,9.019,24]tetracosa-1(16),3(12),4,6,8,10,17,19,21,23-decaen-14-yl)oxy]naphthalen-1-yl]sulfanylnaphthalen-2-yl]oxy-13,15-dioxa-2-thia-14-phosphoniapentacyclo[14.8.0.03,12.04,9.019,24]tetracosa-1(16),3(12),4,6,8,10,17,19,21,23-decaene
• 英文别名: 14-sulfido-14-[1-[2-[(14-sulfido-13,15-dioxa-2-thia-14-phosphoniapentacyclo[14.8.0.03,12.04,9.019,24]tetracosa-1(16),3(12),4,6,8,10,17,19,21,23-decaen-14-yl)oxy]naphthalen-1-yl]sulfanylnaphthalen-2-yl]oxy-13,15-dioxa-2-thia-14-phosphoniapentacyclo[14.8.0.03,12.04,9.019,24]tetracosa-1(16),3(12),4,6,8,10,17,19,21,23-decaene
• CAS: 1034498-38-8
• 化学式: C₆₀H₃₆O₆P₂S₅
• 分子量: 1075.22
• InChiKey: XKKMBPVGECHIED-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  20
• 重原子数：
  73
• 可旋转键数：
  6
• 环数：
  14.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  155
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  14-[1-[2-(13,15-Dioxa-2-thia-14-phosphapentacyclo[14.8.0.03,12.04,9.019,24]tetracosa-1(16),3(12),4,6,8,10,17,19,21,23-decaen-14-yloxy)naphthalen-1-yl]sulfanylnaphthalen-2-yl]oxy-13,15-dioxa-2-thia-14-phosphapentacyclo[14.8.0.03,12.04,9.019,24]tetracosa-1(16),3(12),4,6,8,10,17,19,21,23-decaene 在 sulfur 作用下， 以 甲苯 为溶剂， 反应 16.0h， 以87%的产率得到14-Sulfido-14-[1-[2-[(14-sulfido-13,15-dioxa-2-thia-14-phosphoniapentacyclo[14.8.0.03,12.04,9.019,24]tetracosa-1(16),3(12),4,6,8,10,17,19,21,23-decaen-14-yl)oxy]naphthalen-1-yl]sulfanylnaphthalen-2-yl]oxy-13,15-dioxa-2-thia-14-phosphoniapentacyclo[14.8.0.03,12.04,9.019,24]tetracosa-1(16),3(12),4,6,8,10,17,19,21,23-decaene
  参考文献：
  名称：

  Large-bite bis(phosphite) ligand containing mesocyclic thioether moieties: synthesis, reactivity, group 11 (CuI, AuI) metal complexes and anticancer activity studies on a human cervical cancer (HeLa) cell line

  摘要：

  通过三氯化磷与硫代双（2,2'-萘酚）（1）的反应，得到了大位阻双（膦酰）配体[{(–OC10H6(μ-S)C10H6O–)P{μ-(–OC10H6(μ-S)C10H6O–)}P(–OC10H6(μ-S)C10H6O–)}]（P⁁P）（2）。2与硫和硒的定量反应以良好产率得到了相应的硫属元素化合物[(E)P⁁P(E)]（3，E = S；4，E = Se）。用两当量的[ClAu(SMe2)]与2处理得到了双核配合物[ClAu(P⁁P)AuCl]（5），而1:1反应与CuI则得到了[(P⁁P)CuI]（6）配合物。铜（I）配合物6在与各种吡啶衍生物处理后，产生了混合配体配合物[(P⁁P)CuI(NC5H5)]（7）、[(P⁁P)Cu(2,2'-联吡啶)]I（8）、[(P⁁P)Cu(1,10-菲罗啉)]I（9）和{[(P⁁P)Cu(4,4'-联吡啶)]I}∞（10）。化合物2-5在人宫颈癌细胞（HeLa）系上测试了它们的细胞毒活性。发现化合物2和3显著抑制HeLa细胞的增殖。这些试剂还能诱导癌细胞凋亡。本研究提供的证据表明，化合物2和3在结肠腺癌细胞（HCT-116）系中激活了肿瘤抑制蛋白p53。

  DOI：

  10.1039/b719904j

文献信息

• Large-bite bis(phosphite) ligand containing mesocyclic thioether moieties: synthesis, reactivity, group 11 (CuI, AuI) metal complexes and anticancer activity studies on a human cervical cancer (HeLa) cell line
  作者：D. Suresh、Maravanji S. Balakrishna、Krishnan Rathinasamy、Dulal Panda、Joel T. Mague

  DOI：10.1039/b719904j

  日期：——

  The large-bite bis(phosphite) ligand [(–OC10H6(µ-S)C10H6O–)Pµ-(–OC10H6(µ-S)C10H6O–)}P(–OC10H6(µ-S)C10H6O–)}] (P⁁P) (2) was obtained by the reaction of PCl3 and thiobis(2,2′-naphthol) (1). The stoichiometric reactions of 2 with elemental sulfur and selenium afforded the corresponding chalcogenide derivatives [(E)P⁁P(E)] (3, E = S; 4, E = Se) in good yield. Treatment of two equivalents of [ClAu(SMe2)] with 2 afforded a dinuclear complex [ClAu(P⁁P)AuCl] (5), whereas the 1 : 1 reaction with CuI yielded the [(P⁁P)CuI] (6) complex. The copper(I) complex 6 on treatment with various pyridyl derivatives, produced mixed-ligand complexes [(P⁁P)CuI(NC5H5)] (7), [(P⁁P)Cu(2,2′-bpy)]I (8), [(P⁁P)Cu(1,10-phen)]I (9) and [(P⁁P)Cu(4,4′-bpy)]I}∞ (10). The compounds 2–5 were tested for their cytotoxic activity on the human cervical cancer (HeLa) cell line. Compounds 2 and 3 were found to inhibit proliferation of HeLa cells significantly. These agents also induced apoptotic cell death in cancer cells. Evidence presented in this study indicated that the compounds 2 and 3 activate the tumor suppressor protein p53 in the colon adenocarcinoma (HCT-116) cell line.

  通过三氯化磷与硫代双（2,2'-萘酚）（1）的反应，得到了大位阻双（膦酰）配体[(–OC10H6(μ-S)C10H6O–)Pμ-(–OC10H6(μ-S)C10H6O–)}P(–OC10H6(μ-S)C10H6O–)}]（P⁁P）（2）。2与硫和硒的定量反应以良好产率得到了相应的硫属元素化合物[(E)P⁁P(E)]（3，E = S；4，E = Se）。用两当量的[ClAu(SMe2)]与2处理得到了双核配合物[ClAu(P⁁P)AuCl]（5），而1:1反应与CuI则得到了[(P⁁P)CuI]（6）配合物。铜（I）配合物6在与各种吡啶衍生物处理后，产生了混合配体配合物[(P⁁P)CuI(NC5H5)]（7）、[(P⁁P)Cu(2,2'-联吡啶)]I（8）、[(P⁁P)Cu(1,10-菲罗啉)]I（9）和[(P⁁P)Cu(4,4'-联吡啶)]I}∞（10）。化合物2-5在人宫颈癌细胞（HeLa）系上测试了它们的细胞毒活性。发现化合物2和3显著抑制HeLa细胞的增殖。这些试剂还能诱导癌细胞凋亡。本研究提供的证据表明，化合物2和3在结肠腺癌细胞（HCT-116）系中激活了肿瘤抑制蛋白p53。