Synthesis, In Vitro Evaluation of Some Novel Quinazolin-4(3H)-one Derivatives as Anti-Tumor Agents

Srivalli, K.; Satish, K.

doi:10.7598/cst2012.272

Cited by 5 publications

(4 citation statements)

References 5 publications

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“…The core pyrazolone structure generally attracted widespread attention because of the diversity of biological activity as they showed anti-inflammatory [11][12][13] analgesic, 14,15) antitumor, 16) antimicrobial, 17,18) hypoglycemic, 19) and antitubercular 20) activities. One of the first synthetic organic compounds that used as an important drug and having a pyrazolone nucleus was antipyrine I.…”

Section: -10)mentioning

confidence: 99%

Pyrazolone Derivatives: Synthesis, Anti-inflammatory, Analgesic, Quantitative Structure–Activity Relationship and <i>in Vitro</i> Studies

et al. 2013

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Some 1-(4-chlorophenyl or benzenesulfonamide)-2,3-and/or 4-substituted-1H-pyrazol-5(4H)-one derivatives were synthesized and screened for their anti-inflammatory and analgesic activities, in addition to their ulcerogenic liability. They were found to be active as anti-inflammatory and analgesic agents. Compound 6b was found to be the most active as anti-inflammatory agent and compound 9b was found to be the most active one as anti-inflammatory and analgesic agent. On the other hand, cyclooxygenase-1/-2 (COX-1)/COX-2 isozyme selectivity was also done and the tested compounds showed equal inhibition to both isoforms. Moreover, 2D-quantitative structure-activity relationship (QSAR) studies revealed well predictive and statistically significant and cross validated QSAR model that helps to explore some expectedly potent compounds.Key words pyrazolone; acetic acid; quantitative structure-activity relationship; cyclooxygenase inhibition; anti-inflammatory Non steroidal anti-inflammatory drugs (NSAIDs) were known as important class of therapeutic agents for the alleviation of pain and inflammation. The pharmacological activity of NSAIDs is due to the inhibition of prostaglandins biosynthesis from arachidonic acid through inhibiting cyclooxygenases (COXs).1,2) However, long term use of NSAIDs was associated with several side effects such as gastrointestinal mucosal damage, bleeding, intolerance, and renal toxicity. 3-6)The gastrointestinal (GI) damage from NSAIDs generally attributes to two factors, i.e., local irritation by the carboxylic acid moiety, common to most NSAIDs (topical effect) and decreased tissue prostaglandins production which maintains GI health and homeostasis. Therefore, synthetic approaches based upon chemical modification of NSAIDs were taken with the aim of improving NSAID safety profile. 7-10)The core pyrazolone structure generally attracted widespread attention because of the diversity of biological activity as they showed anti-inflammatory [11][12][13] analgesic, 14,15) antitumor, 16) antimicrobial, 17,18) hypoglycemic, 19) and antitubercular 20) activities. One of the first synthetic organic compounds that used as an important drug and having a pyrazolone nucleus was antipyrine I. 21) In addition, many pyrazolones like aminophenazone II, propyphenazone III, and famorofazone IV (Fig. 1) are widely used as anti-inflammatory, analgesic, and antipyretic drugs. 7,22,23) Besides, different pyrazolones found to possess significant anti-inflammatory activity as compounds V, 24) VI, 11) VII, 11) and VIII 13) (Fig. 2). Thus, our main objective is to design novel pyrazolone derivatives to be further explored as powerful and novel nonulcerogenic anti-inflammatory lead candidates. Some of these derivatives contain acidic centers with further esterification aiming to decrease the local side effects that might be attained by its acidic moieties.The synthesized compounds were evaluated for their antiinflammatory and analgesic activities. Ulcerogenic liability was also performed; in addition, evaluation for the...

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Section: -10)mentioning

confidence: 99%

Pyrazolone Derivatives: Synthesis, Anti-inflammatory, Analgesic, Quantitative Structure–Activity Relationship and <i>in Vitro</i> Studies

et al. 2013

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“… 14 In particular, 2,3-dihydroquinazolinone-4(1 H )-one (DHQ) is the building block of many important therapeutic agents, such as anti-tumor, anti-convulsant, anti-microbial, anti-depressant, anti-viral, etc. 15 In this context, a number of methods have been reported to synthesize 2,3-dihydroquinazolinone-4(1 H )-one derivatives ( Scheme 1 ). The condensation of 2-aminobenzamide with an aldehyde (aryl/alkyl) is a traditional method for synthesizing DHQ derivatives using a variety of catalysts such as Cp 2 TiCl 2 , Y(OTf) 3 , H[Gly 2 B], CAN, TiCl 4 –Zn, CNTs, H 3 PW 12 O 40 , etc.…”

Section: Introductionmentioning

confidence: 99%

Production of a recyclable nanobiocatalyst to synthesize quinazolinone derivatives

et al. 2022

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“…Quinazolin‐4‐one is a heterocyclic scaffold occupying a unique role in the field of medicinal chemistry and represents an important scaffold for designing new bioactive anticancer agents . 2,3‐Disubstituted quinazolin‐4(3 H )‐one I (Fig.…”

Section: Introductionmentioning

confidence: 99%

“…2,3‐Disubstituted quinazolin‐4(3 H )‐one I (Fig. ) was reported to have good anticancer activity , in addition, compound II showed a promising antitumor activity. 2‐(2‐Thieno)‐6‐iodo‐3‐amino‐3,4‐dihydro‐quinazolin‐4‐one III exhibited a remarkable anticancer activity in comparison to the known drug 5‐FU.…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, and Molecular Docking Studies of 2‐(Furan‐2‐yl)quinazolin‐4‐one Derivatives as Potential Antiproliferative Agents

Ahmed

Belal

2015

Archiv der Pharmazie

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Fifteen new derivatives of quinazolin-4-one bearing the 2-furyl moiety at position 2 and a substituted phenyl moiety at position 3 were designed and synthesized to be evaluated as cytotoxic agents. Their chemical structures were confirmed by spectral and elemental analysis; cytotoxic activity evaluation was performed against HEPG2, HCT116, and MCF7 cancer cell lines using the sulforhodamine-B assay. All the tested compounds except 6a showed high potency against the HEPG2 cancer cell line (IC50 8-101 nM/mL); 11 compounds out of 15 proved to be potent against HCT116 cells (IC50 3-49 nM/mL), also 11 of the tested compounds showed high potency against MCF7 cells with IC50 values ranging from 7 to 63 nM/mL. The rest of the tested compounds showed IC50 values of more than 100 nM/mL. Compounds 3e and 4d are the most active compounds against HEPG2 cells; in addition, 3e is the most active compound against MCF7 cells. Also, compounds 4a, 3a, and 3b are the most active compounds against HCT116 cells. Compounds 3a, 3b, 3e, 4a, and 4d were also evaluated for their inhibitory activity against the EGFR tyrosine kinase (EGFR-TK) and showed a percentage inhibitory activity ranging from 53 to 84%. The most potent EGFR-TK inhibitors, 3a (84%), 3b (75%), and 3e (60%), were docked into the ATP binding site of the EGFR to explore their binding mode and possible interactions.

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Synthesis, In Vitro Evaluation of Some Novel Quinazolin-4(3H)-one Derivatives as Anti-Tumor Agents

Cited by 5 publications

References 5 publications

Pyrazolone Derivatives: Synthesis, Anti-inflammatory, Analgesic, Quantitative Structure–Activity Relationship and <i>in Vitro</i> Studies

Pyrazolone Derivatives: Synthesis, Anti-inflammatory, Analgesic, Quantitative Structure–Activity Relationship and <i>in Vitro</i> Studies

Production of a recyclable nanobiocatalyst to synthesize quinazolinone derivatives

Design, Synthesis, and Molecular Docking Studies of 2‐(Furan‐2‐yl)quinazolin‐4‐one Derivatives as Potential Antiproliferative Agents

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