4,4,6,6-tetrachloro-2,2-(2,2-dimethylpropane-1,3-diyldioxy)-1,3,5,2λ⁵,6λ⁵-triazatriphosphorine | 131501-44-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环化合物
• 英文名称: 4,4,6,6-tetrachloro-2,2-(2,2-dimethylpropane-1,3-diyldioxy)-1,3,5,2λ⁵,6λ⁵-triazatriphosphorine
• 英文别名: 4,4,6,6-tetrachloro-2,2-(2,2-dimethylpropane-1,3-dioxy)cyclotriphosphazene；4,4,6,6-Tetrachlorocyclo-2,2-(2,2-dimethylpropane-1,3-dioxy)triphosphazene；2,2,4,4-tetrachloro-9,9-dimethyl-7,11-dioxa-1,3,5-triaza-2λ5,4λ5,6λ5-triphosphaspiro[5.5]undeca-1(6),2,4-triene
• CAS: 131501-44-5
• 化学式: C₅H₁₀Cl₄N₃O₂P₃
• 分子量: 378.887
• InChiKey: UWLHEGMVBJWLJJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  55.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  精胺 、 4,4,6,6-tetrachloro-2,2-(2,2-dimethylpropane-1,3-diyldioxy)-1,3,5,2λ⁵,6λ⁵-triazatriphosphorine 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以42%的产率得到15,15-Dichloro-5-[4-(15,15-dichloro-11,11-dimethyl-9,13-dioxa-1,5,7,14,16-pentaza-6lambda5,8lambda5,15lambda5-triphosphadispiro[5.1.58.36]hexadeca-6,8(14),15-trien-5-yl)butyl]-11,11-dimethyl-9,13-dioxa-1,5,7,14,16-pentaza-6lambda5,8lambda5,15lambda5-triphosphadispiro[5.1.58.36]hexadeca-6,8(14),15-triene
  参考文献：
  名称：

  The new dispirobino and dispiroansa spermine derivatives of cyclotriphosphazenes

  摘要：

  In this study, the crystal structures of the dispiroansa spermine derivatives of cyclotriphosphazene are characterised for the first time. The reaction of spiro-, gem-disubstituted cyclotriphosphazene derivatives, N3P3Cl4R2 [R = NHPh, (HN(CH2)(3)NH)(0.5), (OCH2C(CH3)(2)CH2O)(0.5)], (1-3), with spermine (4), in aprotic solvents such as CH2Cl2 results in a series of dispirobino spermine derivatives of cyclotriphosphazene (5a, 6a, 7), namely spermine bridged compounds. Whereas, in protic solvents such as CHCl3 give, dispiroansa derivatives (8-10) namely tetracyclic cyclotriphosphazene. The new series of dispirobino and dispiroansa spermine derivatives of cyclotriphosphazene (5a, 6a, 7-10) have been characterised by elemental analysis, mass spectrometry, X-ray (for 5a, 8,10) and H-1, P-31 NMR spectroscopies. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2009.12.022
• 作为产物：
  描述：

  戊烷-3,3-二醇 在 六氯环三磷腈 作用下， 以 四氢呋喃 、 吡啶 为溶剂， 生成 4,4,6,6-tetrachloro-2,2-(2,2-dimethylpropane-1,3-diyldioxy)-1,3,5,2λ⁵,6λ⁵-triazatriphosphorine
  参考文献：
  名称：

  2-Hydroxyanthraquinone substituted cyclotriphosphazenes: Synthesis and cytotoxic activities in cancer cell lines

  摘要：

  Scientists continue to synthesize substances that have cytotoxic effects and examine their properties to overcome cancer for a long time. This study is aimed at preparing novel cyclotriphosphazene derivatives and examining their anti-cancer effects. For this purpose, the nucleophilic substitution reactions of 2,2-dimethyl 1,3-propanedioxy substituted cyclotriphosphazenes (3-5) with 2-hydroxyanthraquinone (6) were performed in the presence of cesium carbonate in acetone. Three novel anthraquinone substituted cyclotriphosphazenes (7-9) were obtained from these reactions. The molecular structures of the compounds (7-9) were characterized by MALDI-TOF MS, NMR (P-31 and H-1) and FT-IR spectroscopies. The cytotoxic activities of 2,2-dimethyl 1,3-propanedioxy and anthraquinone substituted cyclotriphosphazenes were investigated. We applied MTT assay to specify whether the all compounds are cytotoxic in the cancer cell lines (MCF-7 / DLD-1) and two non-cancerous cell lines (MCF-12A/CCD-18Co). All cells were incubated with (2.5-40 mu M) concentrations of the compounds for 24 h. The compound 3 and 9 were found to be highly effective against breast cancer and compound 4 was highly effective against colon cancer.

  DOI：

  10.1016/j.ica.2020.120005

文献信息

• New type paraben decorated mono- and dispirocyclotriphosphazene compounds: Synthesis, characterization and DNA binding studies
  作者：Gizem Demir Demirel、Burak Köksal、Fatma Yüksel、Gönül Yenilmez Çiftçi

  DOI：10.1016/j.molstruc.2024.138213

  日期：2024.8

  cancer. This is an area that requires further research. For this purpose, six new and pirocyclotriphosphazene compounds decorated with paraben were synthesized and designed for the first time. Their structures were identified by MALDI-TOF MS, H, P NMR and FT-IR spectroscopy. Moreover, the molecular structure of Compound 8 was determined by X-Ray crystallography. The DNA interaction properties of the

  对羟基苯甲酸酯是一组广泛用于化妆品、制药和食品行业的化学防腐剂。尽管一些研究引起了对与对羟基苯甲酸酯相关的潜在健康风险的担忧，但值得注意的是，肿瘤组织中对羟基苯甲酸酯的存在并不能提供对羟基苯甲酸酯致癌的确凿证据。这是一个需要进一步研究的领域。为此，首次合成并设计了六种新型的对羟基苯甲酸酯修饰的吡环三磷腈化合物。通过MALDI-TOF MS、H、P NMR和FT-IR光谱鉴定了它们的结构。此外，化合物8的分子结构通过X射线晶体学确定。通过琼脂糖凝胶电泳研究了目标分子的 DNA 相互作用特性。
• Effect of gem 2,2′-disubstitution and base in the formation of spiro- and ansa-1,3-propandioxy derivatives of cyclotriphosphazenes
  作者：Aylin Uslu、Simon J. Coles、David B. Davies、Mükremin Esen、Michael B. Hursthouse、Adem Kılıç

  DOI：10.1016/j.ica.2010.07.005

  日期：2010.10

  The gem-dialkyl effect has been investigated in the reactions of cyclotriphosphazene, N3P3Cl6 1, with various 2,2'-derivatives of 1,3-propandiol, CXY(CH2OH)(2), in either THF or DCM to form spiro (6-membered) and ansa (8-membered ring) derivatives. The reactions were made with a number of symmetrically-substituted (X = Y, methyl, ethyl, n-butyl and a malonate ester) and unsymmetrically-substituted (X not equal Y, methyl/H, phenyl/H, methyl/n-propyl, ethyl/n-butyl and Br/NO2) 1,3-propandiols. The products were analysed by H-1 and P-31 NMR spectroscopy and some of the spiro and ansa derivatives were also characterized by X-ray crystallography. Reactions of 1 with unsymmetrically-substituted 1,3-propandiols results in the formation of two structural isomers of ansa-substituted compounds, both isomers (endo and exo) have been structurally-characterized by X-ray crystallography for the ethyl/n-butyl derivative. It is found that the regioselectivity of the reaction is changed when the base is changed. The relative proportions of spiro and ansa compounds formed under different reaction conditions were quantified by P-31 NMR measurements of the reaction mixtures. The results were rationalised mainly in terms of the electronic effect of the substituents, whereas the steric effect has a secondary role in the formation of both spiro and ansa compounds. (C) 2010 Elsevier B.V. All rights reserved.
• Synthesis, cytotoxicity and apoptosis of cyclotriphosphazene compounds as anti-cancer agents
  作者：Tuba Yıldırım、Kemal Bilgin、Gönül Yenilmez Çiftçi、Esra Tanrıverdi Eçik、Elif Şenkuytu、Yıldız Uludağ、Leman Tomak、Adem Kılıç

  DOI：10.1016/j.ejmech.2012.03.018

  日期：2012.6

  In the present study, a number of new dispirobino and dispiroansa spermine derivatives of cyclotriphosphazene (8-10, 13) were synthesized and characterized by elemental analysis, mass spectrometry, H-1 and P-31 NMR spectroscopy. At first, in vitro cytotoxic activity of cyclotriphosphazene compounds (1-14) against HT-29 (human colon adenocarcinoma), Hep2 (Human epidermoid larynx carcinoma), and Vero (African green monkey kidney) cell lines was investigated. Our study showed that most of these compounds stimulate apoptosis and they have cytotoxic effects for HT-29 and Hep2 cells. Additionally, these compounds (1-14) were investigated for their antibacterial activity against gram-positive (Staphylococcus aureus), gram-negative (Escherichia coli, Pseudomonas aeruginosa) bacteria and for their antifungal activity against Candida albicans, and were shown to be inactive. (C) 2012 Elsevier Masson SAS. All rights reserved.
• 4,4,6,6-Tetrachloro-2,2-(2,2-dimethylpropane-1,3-diyldioxy)-1,3,5,2λ⁵,4λ⁵,6λ⁵-triazatriphosphorine
  作者：N. Satish Kumar、K. C. Kumara Swamy

  DOI：10.1107/s0108270101015359

  日期：2001.12.15

  The title spirocyclic compound (alternative name: 2,2,4,4-tetrachloro-9,9-dimethyl-7,11-dioxa-1,3,5-triaza-2 lambda (5) 4 lambda (5),6 lambda (5)-triphosphaspiro[5.5]undeca-1,3,5-triene), C5H10Cl4N3O2P3, does not contain alternating long-short P-N bond lengths in the phosphazene ring [P-N 1.559 (2)-1.596 (2) Angstrom], as are observed in other analogous spirocyclic compounds. The six-membered phosphazene ring has a chair conformation in the solid state, but a conformational equilibrium in solution is indicated by NMR spectroscopy.
• Shaw, Robert A., Phosphorus, Sulfur and Silicon and the Related Elements, 1989, vol. 45, p. 103 - 136
  作者：Shaw, Robert A.

  DOI：——

  日期：——