Novel Quinazoline Derivatives Bearing a Sulfapyridine Moiety as Anticancer and Radiosensitizing Agents

Abstract

Quinazoline derivatives posses many types of biological activities and have recently been reported to show substantial antitumor activity in vitro and/or in vivo. There is a variety of mechanisms for their anticancer activity. The present work reports the possible utility of methyl anthranilate in the synthesis of some new quinazoline derivatives, bearing a substituted sulfonamide moiety. All the newly synthesized compounds were evaluated for their in vitro anticancer activity against human liver cancer cell line, using doxorubicin as a reference drug. In addition, the most active compounds 14 and 15 were selected and evaluated for their ability to enhance the cell killing effect of γ‐radiation.

The Antiproliferative and Apoptotic Effects of a Novel Quinazoline Carrying Substituted-Sulfonamides: In Vitro and Molecular Docking Study

“…IR spectrum of compound 3 exhibited a characteristic band for NH 2 , CH aromatic, C=O, C=N and SO 2 groups. 1 H-NMR spectrum revealed signals at 3.9 ppm assigned to OCH 3 and 12.3 ppm attributed to SH proton. 13 C-NMR showed signals at 55.7 ppm for OCH 3 and 160.9 ppm due to C=O of quinazoline ring.…”

“…IR spectra of 4a-n displayed additional 2NH and 2C=O bands at their assigned regions. 1 H-NMR spectra of 4a-n revealed signals at 3.7-3.9 ppm assigned to OCH 3 , two singlet signals, one at 3.9-4.1 ppm referring to the SCH 2, 4.1-4.3 ppm due to N-CH 2 , and 7.5-8.0 ppm for aromatic protons (AB system), 8.0-8.2 ppm attributed for SO 2 NH proton and 8.8-10.5 ppm for 2NH protons. 13 C-NMR of 4a-n displayed two signals peculiar to the SCH 2 , NCH 2 and 3CO carbons.…”

“…Quinazoline and sulfonamide moieties have been identified as classes of chemotherapeutic agents with substantial therapeutic value against solid tumors [1][2][3][4]. Gefitinib (small-molecule inhibitor) being the original quinazoline molecule to be approved as an antitumor agent for treatment of Non-Small Cell Lung Cancer [5][6][7].…”

6-(2-Morpholinoethyl)-thiazolo[3,2-a]pyrimidin-5-one: A novel scaffold for the synthesis of potential PI3kα inhibitors

“…The discovery of E-7010 [14] and vemurafenib (PLX4032) [15], fused heterocyclic compounds incorporating sulfonamide moiety, emphasized the role of sulfonamides as an important class of anticancer agents which interact with a wide range of different cellular targets. In addition, series of novel compounds containing benzenesulfonamide moiety and incorporating benzoquinones [16], quinazolin-2-ones [17] or coumarins [18] have revealed promising anticancer activities.…”

Synthesis, Anticancer, and QSAR Studies of 2‐Alkyl(aryl,hetaryl)quinazolin‐4(3H)‐thione's and [1,2,4]Triazolo[1,5‐c]quinazoline‐2‐thione's Thioderivatives

“…Moreover, N ‐{4‐[(3‐chlorophenyl)amino]quinazolin‐6‐yl}picolinamide showed anticancer properties at 2.9 μ m against human c‐Src kinases when compared with saracatinib . Benzylideneamino A and 3‐phenylthioureido B derivatives of 4‐(3‐ R ‐3,4‐dihydro‐4‐oxoquinazolin‐2‐ylamino)‐ N ‐(pyridin‐2‐yl)benzenesulfonamide had GI 50 of 22.11 and 19.70 μ m against human liver cell line HEPG2, respectively . Moreover, 2‐(3‐benzyl‐3,4‐dihydro‐6‐iodo‐4‐oxoquinazolin‐2‐ylsulfanyl)acetohydrazide substituted with N ‐propanethione ( C ), N ‐benzyloxo ( D ), and cyclic piperazine‐3,6‐dione ( E ) fragment showed mean graph midpoint GI 50 values of 12.8, 11.3, and 13.8 μ m of nine subpanel anticancer cell lines ( Fig.…”