首页> 外文期刊>Inorganica Chimica Acta >Phosphorus-nitrogen compounds. Part 44. The syntheses of N,N-spiro bridged cyclotriphosphazene derivatives with (4-fluorobenzyl) pendant arms: Structural and stereogenic properties, DNA interactions, antimicrobial and cytotoxic activities
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Phosphorus-nitrogen compounds. Part 44. The syntheses of N,N-spiro bridged cyclotriphosphazene derivatives with (4-fluorobenzyl) pendant arms: Structural and stereogenic properties, DNA interactions, antimicrobial and cytotoxic activities

机译:磷 - 氮化合物。 第44部分。N,N-螺桥桥接环三膦腈衍生物的合成:结构和立体性特性,DNA相互作用,抗菌和细胞毒性活性

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Isopropylaminopentachlorocyclotriphosphazene, (N3P3Cl5(NHCHMe2) (1), containing a P-NH group in the alkyl-chain, gives the NN-spirobridged octachlorobiscyclotriphosphazene, [N3P3Cl4(NCHMe2)](2) (2), in the presence of NaH. The reactions of 2 with excess pyrrolidine result in the formation of the fully substituted bridged product 2a. The reactions of 2 with 1:1 and 1:2 equimolar amounts of N-(4-fluorobenzyl)N'methylethane-1,2-diamine and N-(4-fluorobenzyl)-N'methylpropane-1,3-diamine produce the (4-fluorobenzyl) pendant armed monospiro (2b and 2c) and dispiro (2f and 2g) products. These compounds react with excess pyrrolidine to form stable, fully substituted cyclotriphosphazenes (2d, 2e, 2h and 2i). The structures of 2a and 2f are determined by X-ray crystallography. The stereogenic properties of 2a and 2f having four potential stereogenic P-centers are investigated by crystallography. The monospiro (2b-2e) and dispiro (2f-2i) products have one and two equivalent chiral centers, respectively. The dispiro derivatives may have two meso (trans-trans and cis-cis) and two racemate (trans-cis and cis-trans) mixtures. However, the structure of 2f is found to be as trans-trans (meso) isomer. Besides, in vitro antimicrobial and cytotoxic activities of 2d and 2h are evaluated. The compounds exhibit significant growth inhibitory effects on E. coli and B. cereus bacteria. Compound 2d has high anticancer and apoptotic activities.
机译:Isopropylaminopentachlorocyclotriphosphazene,(N3P3Cl5(NHCHMe2)(1),含有在烷基链上的P-NH基团,给出了NN-spirobridged octachlorobiscyclotriphosphazene,[N3P3Cl4(NCHMe2)](2)(2),在NaH的存在下进行。该用过量的吡咯烷结果在完全取代的桥连的产物2a的形成的2反应2 1所述的反应:1和1:2倍摩尔量的N-(4-氟苄基)N'methylethane -1,2-二胺和N-(4-氟苄基)-N'methylpropane -1,3-二胺制备(4-氟苄基)挂件武装单螺(2b和2c)和二螺(2f和2g)的产品。这些化合物用过量的吡咯烷,以形成稳定的反应,完全取代的cyclotriphosphazenes(2D,2E,2H和2I)。2a的结构和2f由X-射线晶体学确定。2a的和2f具有四个潜在立体P-中心的立体性质由晶体的影响。该单螺(图2b-2e)的和二螺(2F-2I)产品有一个和两个当量的手性中心,respec tively。的二螺衍生物可具有两个内消旋(反式反式和顺式 - 顺式)和两个外消旋体(反式 - 顺式和顺式 - 反式)的混合物。然而,2f的结构被发现是作为反式 - 反(内消旋)异构体。此外,在体外抗微生物和2d中细胞毒活性和2h进行评估。化合物表现出对大肠杆菌和蜡状芽孢杆菌的细菌显著生长抑制效果。化合物2d具有高的抗癌和细胞凋亡活性。

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