Preliminary communication Synthesis and biological properties of 4-(3H )-quinazolone derivatives Anjani K. Tiwari a,b , Vinay Kumar Singh b , Aruna Bajpai b , Gauri Shukla a , Sweta Singh a , Anil K. Mishra a, * a Nanotech and Stem Cell Research, Division of Radiopharmaceuticals, Institute of Nuclear Medicine and Allied Sciences, Brig. S.K. Mazumdar Road, Delhi-110054, India b Department of Chemistry, Lucknow University, Lucknow-226007, India Received 25 October 2006; received in revised form 6 January 2007; accepted 8 January 2007 Available online 20 January 2007 Abstract A new quinazolone series has been designed, and synthesized by the anthranilic acid and different acid derivatives. Their structures have been elucidated on the basis of elemental analyses and spectral studies (IR, 1 H NMR, FT-IR and FAB-MS). A preliminary radiolabelling study with technetium has shown a very good future prospect for further evaluation in vivo. The biological activities (antifungal, antibacterial as well as anticancerous) of the evaluated compounds are discussed in this article. Ó 2007 Elsevier Masson SAS. All rights reserved. Keywords: Analogues; Spectroscopic; Antifungal; Antibacterial; Anticancerous 1. Introduction Quinazolone and their derivatives are building block for approximately 150 naturally occurring alkaloids isolated from a number of families of the plant kingdom, from microorgan- isms and animals [1e4] and are now known for a wide range of biological properties including hypnotic, sedative, analgesic, anticonvulsant, antibacterial, antidiabetic, anti-inflammatory, anti-tumor and several other useful and interesting properties [5e13]. In addition, some derivatives are calcium antagonists and share the common property of interfering with the influx of extracellular calcium via the calcium L channel [14]. Recently quinozolone chemistry has got new direction due to some resemblance with folic acid [15e17]. So keeping this fact in mind that quinazolone as very important moiety, we have synthesized a bis series of quinazolone having different substituents (according to our previous work [12]) in good yield and after that screened them for in vivo microbial activity. 2. Results and discussion All the final compounds 4AeD were prepared in good yields. The physical parameters of these compounds are men- tioned in Table 1 and the synthetic route is shown in Scheme 1. All intermediate as well as final quinazolone analogues are an- alyzed by different spectroscopic technique such as UV, IR, NMR, mass spectroscopy and by elemental analysis. The spec- tral evidences confirm the presence of eNeC]O, eNHeNeC and fused ring system (IR at 3330, 1685, 1460 cm 1 ). Sim- ilarly, NMR multiplet in the range of 6.7e8 ppm of 15e25 hydrogens also confirms the presence of aromatic rings. Ami- nobenzoic acid with excess equivalent of benzoyl chloride in the presence of a base particularly an organic base like pyr- idine affords 2-phenyl-4-oxo-3,1-benzoxazine (2) in excellent yield. It is thought that initially N-benzoyl anthranilic acid is formed which undergoes tautomerization and subsequent cyclization in the presence of pyridine .In the presence of * Corresponding author. House no 1480 (Third floor), Outram Lines, Near Kingsway Camp, Delhi-110054, India. Tel.: þ911123905117; fax: þ911123919509. E-mail addresses: akmishra@inmas.org, mis_ak@rediffmail.com (A.K. Mishra). 0223-5234/$ - see front matter Ó 2007 Elsevier Masson SAS. All rights reserved. doi:10.1016/j.ejmech.2007.01.002 European Journal of Medicinal Chemistry 42 (2007) 1234e1238 http://www.elsevier.com/locate/ejmech