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

Abstract

Considering the frightening high level of mortality from cancer, studies of anticancer agents are vital nowadays. The 24 thioderivatives of 2‐alkyl(aryl)‐quinazolin‐4(3H)‐thiones and 20 thioderivatives of [1,2,4]triazolo[1,5‐c]quinazoline‐2‐thiones were synthesized and evaluated for preliminary in vitro anticancer activity with subsequent in silico QSAR analysis. The substance 18 had the best results inhibiting growth of eight cancer cell lines: CCRF‐CEM of leukemia; SF‐539, SNB‐75, and U251 of CNS cancer; 786, RXF393, and UO‐31 of renal cancer; and MDA‐MB‐231/ATCC of breast cancer (−31.50 – 47.41% of cell growth) with low procancer effect. Calculated QSAR‐models for CCRF‐CEM of leukemia, T‐47D and HS 578T of breast cancer, and mean cell growth demonstrated good rate of anticancer activity prediction (r2 = 0.7 – 0.8, QnormalLOO2 = 0.5 – 0.7).

Application of Azide-Tetrazole Tautomerism and Arylsulfanyl Group Dance in the Synthesis of Thiosubstituted Tetrazoloquinazolines

“…Product was washed with hot EtOH (2 × 4 mL); Method A, yield: 0.35 g (81% from 0.29 g, 1.0 mmol of 2c); Method B, yield: 0.46 g (62%); colorless solid; R f = 0. 16…”

“…The importance of thioquinazoline derivatives has increased lately. Potential antibacterial, 10,11 antimicrobial, 12 antiviral, 13 antitumor, [14][15][16][17] bronchodilatory 18 activity, and monoamine oxidase inhibitor activity, 19 which is important for the treatment of Parkinson's disease were found among 2-substituted 4(3H)-quinazoline-4-thiones, substituted 2-thioquinazolin-4-one analogues, and unsubstituted or 2-substituted 4-thioquinazolines. Compounds from the 4-thioquinazoline series are also known as agriculture antimicrobials.…”

PIFA Mediated Synthesis of Bis‐1,2,4‐triazoloquinazolines as Potential Anticancer Agents on MCF‐7 Cancer Cells: Characterization, Molecular Docking, Antiproliferative and ADME Profile

“…Fungicide (fluquinconazole), and antifungal (albaconazole) are representative of blockbuster drugs that contain both quinazoline and 1,2,4-triazole nuclei, and recently, U.S. FDA has approved a quinazoline hybrid 1,2,4-triazole based anticancer drug (tucatinib), which is mainly utilized for the treatment of metastatic HER2-positive breast cancer [16] (Figure 1). Furthermore, literature survey described the 1,2,4-triazoloquinazolines as a central core, enriched with diverse and therapeutically bewitching bioactivities, such as anticancer, [17] antimicrobial, [18] antioxidant, [19] antihypertensive, [20] anticonvulsant, [21] antihistaminic, [22] anticonvulsant, [23] antitoxoplasmosis, [24] and antidepressant [25] etc. Shahenda and coworkers [26] in 2020, investigated the cytotoxicity potential of several [1,2,4]-triazolo[4,3-c]quinazolines based compounds for in vitro antitumor activity against five different cancer cell lines and in vitro EGFR-TK inhibitory activity.…”

Quinazoline-containing Hydrazydes of Dicarboxylic Acids and Products of Their Structural Modification: A Novel Class of Anti-inflammatory Agents

“…[1][2][3][4][5][6][7] Moreover, cyclisation of above-mentioned hydrazides yielded substituted triazolo [c]quinazolines that show a wide range of biological activity including anticonvulsant, antitumor, hypoglycemic, antibacterial and other activities. [8][9][10][11][12][13][14][15][16][17][18][19][20][21] Despite the numerous publications devoted to the chemistry and biology of hydrazides formed by quinazolin-4(3H)-ylidenehydrazine, some features of their formation, reactivity, physicochemical and biological properties have been insufficiently studied. One of the promising directions of studies is the synthesis and further cyclization of hydrazides formed by quinazolin-4(3H)-ylidenehydrazine and dicarboxylic acids or their monoesters.…”