Exploring a solvated dimer of Gefitinib: a quantitative analysis

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dc.contributor.author Angira, Deekshi
dc.contributor.author Shaik, Althaf
dc.contributor.author Kirubakaran, Sivapriya
dc.contributor.author Thiruvenkatam, Vijay
dc.date.accessioned 2018-08-23T05:49:50Z
dc.date.available 2018-08-23T05:49:50Z
dc.date.issued 2018-08
dc.identifier.citation Angira, Deekshi; Shaik, Althaf; Kirubakaran, Sivapriya and Thiruvenkatam, Vijay, "Exploring a solvated dimer of Gefitinib: a quantitative analysis", Acta Crystallographica Section C: Structural Chemistry, DOI: 10.1107/S2053229618009671, vol. 74, no. 8, Aug. 2018. en_US
dc.identifier.issn 2053-2296
dc.identifier.uri http://dx.doi.org/10.1107/S2053229618009671
dc.identifier.uri https://repository.iitgn.ac.in/handle/123456789/3853
dc.description.abstract Gefitinib or Iressa is an orally administered anilinoquinazoline used in cancer chemotherapy for the treatment of lung and breast cancer. It is reported to exist in two polymorphic forms, a stable form I and a metastable form II. Both of the forms belong to the triclinic P\overline{1} space group. In this work, we report the crystallization of Gefitinib to form a methanol solvate [systematic name: N-(3-chloro-4-fluoro­phen­yl)-7-meth­oxy-6-[3-(morpholin-4-yl)prop­oxy]quinazolin-4-amine methanol hemisolvate, C22H24ClFN4O3·0.5CH3OH] that was theoretically and experimentally investigated. The unit cell is composed of two independent Gefitinib mol­ecules (A and B) that form a stable mol­ecular complex with methanol in the crystal lattice. To understand the crystal lattice stabilization, a combination of techniques, namely X-ray diffraction, IR spectroscopy, thermogravimetric/differential scanning calorimetry (TG-DSC), Hirshfeld surface analysis and CLP-PIXEL methods were used. The analysis of the crystal structure of this dimer revealed a three-dimensional isostructurality with the already reported form II. The A and B mol­ecules are connected via trifurcated C—H...O and N—H...O hydrogen bonding. In addition, the presence of the methanol mol­ecule stabilizes the crystal structure via C—H...O, N—H...O and C—H...Cl inter­actions between the two monomers. The IR analysis of the dimer has shown characteristic fingerprint values when compared to the commercial form. The TG-DSC analysis of the solvated dimer is in good agreement with the patent reporting cocrystals of Gefitinib. Finally, theoretical calculations by the CLP-PIXEL method and Hirshfeld surface and two-dimensional (2D) fingerprint plot analysis were carried out in order to qu­antify the different inter­molecular inter­actions and their energies in the crystal packing.
dc.description.statementofresponsibility by D. Angira, A. Shaik, S. Kirubakaran and V. Thiruvenkatam
dc.format.extent vol. 74, no. 8
dc.language.iso en en_US
dc.publisher International Union of Crystallography en_US
dc.subject Gefitinib en_US
dc.subject solvated dimer en_US
dc.subject crystal structure en_US
dc.subject Hirshfeld surface en_US
dc.subject CLP-PIXEL en_US
dc.subject drug discovery en_US
dc.subject drug development en_US
dc.subject tyrosine kinase inhibitor en_US
dc.subject solvatomorph en_US
dc.subject polymorphism en_US
dc.title Exploring a solvated dimer of Gefitinib: a quantitative analysis en_US
dc.type Article en_US
dc.relation.journal Acta Crystallographica Section C: Structural Chemistry

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