diaquabis(η²-O,O'-indomethacin)zinc(II)

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: diaquabis(η²-O,O'-indomethacin)zinc(II)
• 英文别名: ZINC;2-[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetate;dihydrate
• 化学式: C₃₈H₃₄Cl₂N₂O₁₀Zn
• 分子量: 814.991
• InChiKey: FJZKDTJRBUIUBI-UHFFFAOYSA-L

计算性质

• 辛醇/水分配系数(LogP)：
  3.53
• 重原子数：
  53
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  145
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2,2'-联吡啶 、 diaquabis(η²-O,O'-indomethacin)zinc(II) 以 乙腈 为溶剂， 反应 16.0h， 以77%的产率得到Zn(indomethacin)₂(2,2'-bipyridine)
  参考文献：
  名称：

  Polypyridyl Zinc(II)-Indomethacin Complexes with Potent Anti-Breast Cancer Stem Cell Activity

  摘要：

  癌症干细胞（CSCs）被认为是肿瘤中临床相关的亚群体，部分负责癌症复发和转移。旨在发现抗CSC药剂的研究计划主要集中在生物制剂和纯有机分子上。最近，我们展示了一类含酚并啉基配体和非甾体抗炎药（NSAIDs）如吲哚美辛的氧化还原活性铜（II）配合物家族，能够有效选择性地杀死乳腺CSCs。在此，我们提出了类似的氧化还原不活性的锌（II）-酚并啉-吲哚美辛配合物，具有与同等浓度下相等的杀死乳腺CSCs和大量乳腺癌细胞的能力（在亚微米或微米范围内）。理论上，一次剂量的锌（II）配合物可以用于消除整个肿瘤人群。令人兴奋的是，其中一些锌（II）配合物对乳腺球体的生长和生存能力的降低程度与已知能有效杀死乳腺CSCs的化合物沙利霉素相当甚至更高。据我们所知，这是第一个研究含锌（II）化合物的抗乳腺CSC活性的报告。

  DOI：

  10.3390/molecules23092253
• 作为产物：
  描述：

  水 、 zinc(II) acetate dihydrate 、 吲哚美辛 以 sodium hydroxide 、 水 为溶剂， 以89.3%的产率得到diaquabis(η²-O,O'-indomethacin)zinc(II)
  参考文献：
  名称：

  Syntheses and Characterization of Anti-inflammatory Dinuclear and Mononuclear Zinc Indomethacin Complexes. Crystal Structures of [Zn₂(Indomethacin)₄(L)₂] (L = N,N-Dimethylacetamide, Pyridine, 1-Methyl-2-pyrrolidinone) and [Zn(Indomethacin)₂(L₁)₂] (L₁ = Ethanol, Methanol)

  摘要：

  The syntheses and spectral and structural characterizations of Zn(II) indomethacin [1-(4-chlorobenzoyl)-5-methoxy2-methyl-1H-indole-3-acetic acid = IndoH] complexes, as different solvent adducts, have been studied. The complexes are unusual in that both monomeric and dimeric complexes are formed and that this is the first example of the same carboxylato ligand binding via both carboxylate oxygen atoms in monomeric and dimeric Zn(II) complexes. The crystal structures of Zn-Indo complexes with N,N-dimethylacetamide (DMA), pyridine (Py), 1-methyl-2-pyrrolidinone (NMP), EtOH, and MeOH as solvent ligands, [Zn-2(Indo)(4)(DMA)(2)]. 2DMA, 1, [Zn-2(Indo)(4)(Py)(2)]. 2H(2)O, 2b, [Zn-2(Indo)(4)(NMP)(2)], 3, cis-[Zn(Indo)(2)(EtOH)(2)], 4, and cis-[Zn(Indo)(2)(MeOH)(2)], 5, were determined. Complexes I, 2b, and 3 crystallize in the triclinic space group P (1) over bar (No. 2): a = 13.628(2) Angstrom, b = 17.462(2) Angstrom, c = 11.078(1) Angstrom, alpha = 99.49(1)degrees, beta = 108.13(1)degrees, gamma = 110.10(1)degrees for 1; a = 13.347(3), b = 16.499(5) Angstrom, c = 10.857(1) Angstrom, alpha = 99.48(2)degrees, beta = 108.25(2)degrees, gamma = 106.24(2)degrees for 2; a = 14.143(3) Angstrom, b = 14.521(2) Angstrom, c = 11.558(2) Angstrom, alpha = 109.07(1)degrees, beta = 90.80(2)degrees, gamma = 116.40(1)degrees for 3. The three complexes exhibit dinuclear paddle-wheel structures with a Zn ... Zn distance of 2.9686(6) Angstrom, Zn-O-RCOO distances of 2.035(2)-2.060(2) Angstrom, and a Zn-O-DMA distance of 1.989(2) Angstrom in 1, a Zn ... Zn distance of 2.969(1) Angstrom, Zn-O-RCOO distances of 2.020(3)-2.049(3) Angstrom, and a Zn-N-Py distance of 2.036(3) Angstrom in 2, and a Zn ... Zn distance of 2.934(1) Angstrom, Zn-O-RCOO distances of 2.009(3)-2.051(3) Angstrom, and a Zn-O-NMP distance of 1.986(3) Angstrom in 3. In these cases, the zinc ions are offset along the z direction such that the L-Zn ... Zn-L moiety is nonlinear, unlike the Cu analogues. Each Zn has a square-pyramidal geometry bridged by four carboxylato ligands in the basal plane with the solvent ligands containing an O- or N-donor atom at the apex. Complexes 4 and 5 are isostructural, with space group C2/c (No. 15). For 4, a = 30.080(2) Angstrom, b = 5.3638(6) Angstrom, c = 24.739(2) Angstrom, beta = 90.342(7)degrees and for 5, a = 29.419(2) Angstrom, b = 5.320(2) Angstrom, c = 24.461(2) Angstrom, beta = 90.840(4)degrees. The Zn resides on a 2-fold axis and the complexes have a distorted cis octahedral structure with Zn-O-RCOO bond lengths of 2.183(3) and 2.169(3) Angstrom, a Zn-O-EtOH bond length of 2.015(3) Angstrom in 4, Zn-O-RCOO bond lengths of 2.195(2) and 2.151(2) Angstrom, and a Zn-O-MeOH bond length of 2.022(3) Angstrom in 5.

  DOI：

  10.1021/ic991477i