Crystal structure and Hirshfeld surface analysis of a salt of antineoplastic kinase inhibitor vandetanib.

IF 0.7 4区化学 Q4 CHEMISTRY, MULTIDISCIPLINARY

Acta Crystallographica Section C Structural Chemistry Pub Date : 2024-03-01 Epub Date: 2024-02-07 DOI:10.1107/S2053229624000676

Haiwu Yang, Minyi Liang, Fang Tian

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Abstract

A salt of vandetanib, namely, 4-({4-[(4-bromo-2-fluorophenyl)amino]-6-methoxyquinazolin-7-yl}methoxy)-1-methylpiperazin-1-ium 2-(butylamino)-4-phenoxy-6-sulfamoylbenzoate acetonitrile monosolvate, C₂₂H₂₅BrFN₄O₂⁺·C₁₇H₁₉N₂O₅S^-·C₂H₃N, composed of kinase inhibitor vandetanib and sulfamyl diuretic bumetanide in a 1:1 molar ratio, is reported. There is proton transfer between the piperidine ring of vandetanib and the carboxyl group of bumetanide to form the salt. In the vandetanib cation, the arene and pyrimidine rings are not coplanar, their planes subtending a dihedral angle of 60.47 (14)°. The roles of the intermolecular interactions in the crystal packing were clarified using Hirshfeld surface analysis, and two-dimensional fingerprint plots indicate that the most important contributions to the crystal packing are from H...H (40.5%), O...H/H...C (20.7%), C...H/ H...C (18.8%) and N...C/C...N (9.0%) contacts.

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抗肿瘤激酶抑制剂凡德他尼的一种盐的晶体结构和 Hirshfeld 表面分析。

一种凡德他尼的盐，即 4-({4-[(4-溴-2-氟苯基)氨基]-6-甲氧基喹唑啉-7-基}甲氧基)-1-甲基哌嗪-1-鎓 2-(丁氨基)-4-苯氧基-6-氨基磺酰基苯甲酸盐乙腈单溶体、C22H25BrFN4O2+-C17H19N2O5S--C2H3N，由激酶抑制剂凡德他尼和磺酰胺基利尿剂布美他尼按 1：摩尔比为 1 的化合物。凡德他尼的哌啶环和布美他尼的羧基之间存在质子转移，从而形成盐。在凡德他尼阳离子中，炔环和嘧啶环不是共面的，它们的平面成 60.47 (14)° 的二面角。利用 Hirshfeld 表面分析法明确了分子间相互作用在晶体堆积中的作用，二维指纹图显示，对晶体堆积贡献最大的是 H...H（40.5%）、O...H/H...C（20.7%）、C...H/ H...C（18.8%）和 N...C/C...N（9.0%）接触。

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来源期刊

Acta Crystallographica Section C Structural Chemistry CHEMISTRY, MULTIDISCIPLINARYCRYSTALLOGRAPH-CRYSTALLOGRAPHY

CiteScore

1.60

自引率

12.50%

发文量

148

期刊介绍： Acta Crystallographica Section C: Structural Chemistry is continuing its transition to a journal that publishes exciting science with structural content, in particular, important results relating to the chemical sciences. Section C is the journal of choice for the rapid publication of articles that highlight interesting research facilitated by the determination, calculation or analysis of structures of any type, other than macromolecular structures. Articles that emphasize the science and the outcomes that were enabled by the study are particularly welcomed. Authors are encouraged to include mainstream science in their papers, thereby producing manuscripts that are substantial scientific well-rounded contributions that appeal to a broad community of readers and increase the profile of the authors.