(SP-4-2)-amminechloro(pyridin-2-yl-acetato-N,O)platinum(II) | 252211-92-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: (SP-4-2)-amminechloro(pyridin-2-yl-acetato-N,O)platinum(II)
• 英文别名: SP-4,2-[PtCl(NH3)(pyridin-2-ylacetato-N,O)]；azane;chloroplatinum(1+);2-pyridin-2-ylacetate
• CAS: 252211-92-0；252212-31-0
• 化学式: C₇H₉ClN₂O₂Pt
• 分子量: 383.694
• InChiKey: LARBYWDZCWBNLY-UHFFFAOYSA-L

计算性质

• 辛醇/水分配系数(LogP)：
  -3.46
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  54
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-乙酰-L-蛋氨酸 、 (SP-4-2)-amminechloro(pyridin-2-yl-acetato-N,O)platinum(II) 以 重水 为溶剂， 生成 SP-4,3-[Pt(N-acetyl-L-methionine-S)(pyridin-2-ylacetato-N,O)(NH3)](1+)
  参考文献：
  名称：

  Pyridine-Carboxylate Complexes of Platinum. Effect of N,O-Chelate Formation on Model Bifunctional DNA−DNA and DNA−Protein Interactions

  摘要：

  This paper reports on the chemistry of platinum complexes containing bidentate pyridine-carboxylate (pyAc = pyridin-2-yl-acetate and picEt = pyridine-2-ethylcarboxylate, ethylpicolinate) (N,O) ligands. The pyridine-2-acetate and ethylpicolinate ligands form six- and five-membered chelates, respectively, upon formation of the Pt-carboxylate bond. In all reactions with picEt with various platinum complex starting materials, spontaneous de-esterification of the pendant carboxylate ester occurs to give directly the chelates K[PtCl2(pic-N,O)]-trans-[Pt(pic-N,O)(2)] and SP- 4,2-[PtCl(pic-N,O)(NH3)] without any evidence of intermediates. The de-esterification is solvent dependent, and molecular modeling was used to explain this reaction. The reactions of the geometric isomers of [PtCl(pyAc-N,O)(NH3)) with 5'-guanosine monophosphate, 5'-GMP, and N-acetyl-L-methionine, AcMet, were investigated by NMR spectroscopy. The objective was to ascertain by model chemistry the feasibility of formation of ternary DNA-Pt-protein adducts in biology. Model nucleotide and peptide compounds were formed in situ by chloride displacement giving (PtL(pyAc-N,O)(NH3)](+) (L = 5'-GMP or AcMet). Competitive reactions were then examined by addition of the complementary ligand L. Sulfur displacement of coordinated 5'-GMP was slow. For SP-4,3-[Pt(AcMet)(NH3)-(PyAc-N,O)](+), a rapid displacement of the sulfur ligand by 5'-GMP was observed, giving SP-4,2-[Pt(5'-GMP-N7)-(pyAc-N,O)(NH3)](+).

  DOI：

  10.1021/ic050062w
• 作为产物：
  描述：

  (SP-4-1)-amminedichloro(pyridin-2-yl-acetic acid-N)platinum(II) monohydrate 在 Na₂HPO₄ 作用下， 以 水 为溶剂， 以66%的产率得到(SP-4-2)-amminechloro(pyridin-2-yl-acetato-N,O)platinum(II)
  参考文献：
  名称：

  顺式几何结构对细胞毒性的反演，该结构对包含二齿N，O-供体吡啶-2-基乙酸盐的结构新颖的铂（II）配合物具有细胞毒性。

  摘要：

  合成了水溶性铂（II）配合物，其中包含N，O-螯合物吡啶-2-基乙酸盐（PyAc）作为铂抗肿瘤配合物中的新型结构基序。反式铂络合物反式-[PtCl（PyAc-N，O）（NH3）]（2）（N-供体是反式）及其异构体顺式-[PtCl（PyAc-N，O）（NH3）]（4 ）（N反式至Cl）分别使用双齿配体由反式[PtCl2（（NH3）（PyAcH）]。H2O（1.H2O）和顺式[PtCl2（NH3）（PyAcMe）（3）制备即使在低pH值和存在额外氯化物的情况下，也容易由各自的二氯物种形成2和4，表明PyAc螯合环具有很高的热力学稳定性，其中1.H2O和2-4为用1H NMR和IR光谱及元素分析对其进行表征，确定了2的固态结构：三斜晶系，P1（编号2），a = 8.170（2）A，b = 9。274（3）A，c = 7.374（2）A，alpha = 108.68（2）度，beta = 113.27（2）度，gamma

  DOI：

  10.1021/ic991259p

文献信息

• Pyridine-Carboxylate Complexes of Platinum. Effect of <i>N</i>,<i>O</i>-Chelate Formation on Model Bifunctional DNA−DNA and DNA−Protein Interactions
  作者：Susana M. O. Quintal、Yun Qu、Adorácion G. Quiroga、Joseph Moniodis、Helena I. S. Nogueira、Nicholas Farrell

  DOI：10.1021/ic050062w

  日期：2005.7.1

  This paper reports on the chemistry of platinum complexes containing bidentate pyridine-carboxylate (pyAc = pyridin-2-yl-acetate and picEt = pyridine-2-ethylcarboxylate, ethylpicolinate) (N,O) ligands. The pyridine-2-acetate and ethylpicolinate ligands form six- and five-membered chelates, respectively, upon formation of the Pt-carboxylate bond. In all reactions with picEt with various platinum complex starting materials, spontaneous de-esterification of the pendant carboxylate ester occurs to give directly the chelates K[PtCl2(pic-N,O)]-trans-[Pt(pic-N,O)(2)] and SP- 4,2-[PtCl(pic-N,O)(NH3)] without any evidence of intermediates. The de-esterification is solvent dependent, and molecular modeling was used to explain this reaction. The reactions of the geometric isomers of [PtCl(pyAc-N,O)(NH3)) with 5'-guanosine monophosphate, 5'-GMP, and N-acetyl-L-methionine, AcMet, were investigated by NMR spectroscopy. The objective was to ascertain by model chemistry the feasibility of formation of ternary DNA-Pt-protein adducts in biology. Model nucleotide and peptide compounds were formed in situ by chloride displacement giving (PtL(pyAc-N,O)(NH3)](+) (L = 5'-GMP or AcMet). Competitive reactions were then examined by addition of the complementary ligand L. Sulfur displacement of coordinated 5'-GMP was slow. For SP-4,3-[Pt(AcMet)(NH3)-(PyAc-N,O)](+), a rapid displacement of the sulfur ligand by 5'-GMP was observed, giving SP-4,2-[Pt(5'-GMP-N7)-(pyAc-N,O)(NH3)](+).
• Inversion of the Cis Geometry Requirement for Cytotoxicity in Structurally Novel Platinum(II) Complexes Containing the Bidentate N,O-Donor Pyridin-2-yl-acetate
  作者：Ulrich Bierbach、Michal Sabat、Nicholas Farrell

  DOI：10.1021/ic991259p

  日期：2000.5.1

  characterized by 1H NMR and IR spectroscopy and elemental analyses. The solid-state structure of 2 was determined: triclinic, P1 (no. 2), with a = 8.170(2) A, b = 9.274(3) A, c = 7.374(2) A, alpha = 108.68(2) degrees, beta = 113.27(2) degrees, gamma = 74.40(2) degrees, V = 479.7(6) A3, Z = 2. The six-membered metallacyclus in 2 adopts a "boat" form, allowing a strainless coordination of platinum. The most promising

  合成了水溶性铂（II）配合物，其中包含N，O-螯合物吡啶-2-基乙酸盐（PyAc）作为铂抗肿瘤配合物中的新型结构基序。反式铂络合物反式-[PtCl（PyAc-N，O）（NH3）]（2）（N-供体是反式）及其异构体顺式-[PtCl（PyAc-N，O）（NH3）]（4 ）（N反式至Cl）分别使用双齿配体由反式[PtCl2（（NH3）（PyAcH）]。H2O（1.H2O）和顺式[PtCl2（NH3）（PyAcMe）（3）制备即使在低pH值和存在额外氯化物的情况下，也容易由各自的二氯物种形成2和4，表明PyAc螯合环具有很高的热力学稳定性，其中1.H2O和2-4为用1H NMR和IR光谱及元素分析对其进行表征，确定了2的固态结构：三斜晶系，P1（编号2），a = 8.170（2）A，b = 9。274（3）A，c = 7.374（2）A，alpha = 108.68（2）度，beta = 113.27（2）度，gamma