CRYSTAL AND MOLECULAR STRUCTURES OF 1-ALKYL-QUINAZOLIN-4(3H)-ONES WITH p-CHLOROPHENYL FRAGMENT

Abstract

Quinazolin-4(3H)-one and quinazoline-2,4-dione cores represent key pharmacophores widely encountered in medicinal chemistry and materials science [1,2]. We present the crystal structures of three novel 4-chlorophenyl quinazolinones: 3-(4-chlorophenyl)-1-heptylquinazoline-2,4(1H,3H)-dione (I), 3-(4-chlorophenyl) -1-isobutylquinazoline-2,4(1H,3H)-dione (II), and 1-benzyl-3-(4-chlorophenyl) quinazoline-2,4(1H,3H)-dione (III). Refinement against single-crystal X-ray data using NoSpherA2 [3] with non-spherical atomic scattering factors overcame standard independent atom model (IAM) limitations. Tailor-made quantum chemical wavefunctions improved refinement statistics (R1, wR2; see Table), produced physically meaningful bond lengths, minimized residual electron density, and enabled precise characterization of hydrogen-bonding networks and crystal packing. Crystallographic data for I–III (CCDC 2579374, 2579373, 2579371) are available free from the CCDC: www.ccdc.cam.ac.uk/data_request/cif.

References

1. Kalpana Singh, P.P. Sharma, A. Kumar, Anurag Chaudhary, R.K. Roy. (2013). 4-Aminoquinazoline Analogs: A Novel Class of Anticancer Agents.Mini-Reviews in Medicinal Chemistry.[Crossref]
2. Prashant S. Auti, Ginson George, Atish T. Paul. (2020). Recent advances in the pharmacological diversification of quinazoline/quinazolinone hybrids.RSC Advances.[Crossref]
3. Kleemiss et al., Chemical Science. 2021, 12(5), 1675–1692.

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