Synthesis and <i>in vitro</i> antitumor and antimicrobial activity of some 2,3-diaryl-7-methyl-4,5,6,7-tetrahydroindazole and 3,3a,4,5,6,7-hexahydroindazole derivatives

Faidallah, Hassan M.; Khan, Khalid Ali; Rostom, Sherif A. F.; Asiri, Abdullah M.

doi:10.3109/14756366.2011.653354

Cited by 17 publications

(3 citation statements)

References 28 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Yield: (19). Yield: (21)(22)(23). To a solution of the appropriate nicotinonitriles 1-5 (20 mmol) in dry acetone (30 mL), a solution of benzoyl isothiocyanate (1.65 g, 20 mmol) in dry acetone (10 mL) was added.…”

Section: 7-disubstituted Pyrido[23-d]pyrimidine-4(3h)-onesmentioning

confidence: 99%

“…During our current interest in exploring new lead structures that possess chemotherapeutic potential, much attention was focused on the antimicrobial and anticancer activities of some pyridine derivatives [18][19][20][21][22][23][24], particularly those possessing the 4,6-disubstituted-2-aminopyridin-3-carbonitrile (nicotinonitriles) scaffold which revealed favourable broad spectrum anticancer and/or antimicrobial efficacy. The collected results persuaded the design and synthesis of novel polysubstituted nicotinonitriles and some derived pyrido [2,3-d]pyrimidines incorporating different functional groups that are claimed to account for the bioactivity of related antitumor and antimicrobial candidates.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Synthesis of Some Polysubstituted Nicotinonitriles and Derived Pyrido[2,3-d]pyrimidines asIn VitroCytotoxic and Antimicrobial Candidates

Faidallah

Rostom

Khan

2016

Journal of Chemistry

Self Cite

View full text Add to dashboard Cite

The synthesis of polysubstituted pyridines, in addition to some derived pyrido[2,3-d]pyrimidine ring systems supported with chemotherapeutically active functionalities, is described. They were evaluated for theirin vitrocytotoxic effects against three different human tumor cell lines (human colon carcinoma HT29, hepatocellular carcinoma Hep-G2, and Caucasian breast adenocarcinoma MCF7). Nine compounds displayed variable cytotoxic potential, among which alkylthio analogs33,34, and37emerged as the most active members, being almost twice as active as doxorubicin against the colon carcinoma HT29 cell line. In addition, the same three analogs showed a clear differential cytotoxic profile as they exhibited a marginal inhibitory effect on the growth of the normal nontransformed human foreskin fibroblast Hs27 cell line. Meanwhile, nineteen compounds were able to exhibit significant antibacterial activity against both Gram-positive and Gram-negative bacteria, together with moderate antifungal activities. The pyrido[2,3-d]pyrimidine-2(1H)-thione30together with its alkylthio derivatives33and34stemmed as the most active antimicrobial members being equipotent to ampicillin againstS. aureus,E. coli,andP. aeruginosa,together with a noticeable antifungal activity againstC. albicans.Compounds33and34could be considered as a promising template for possible dual antimicrobial-anticancer candidates.

show abstract

Section: 7-disubstituted Pyrido[23-d]pyrimidine-4(3h)-onesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis of Some Polysubstituted Nicotinonitriles and Derived Pyrido[2,3-d]pyrimidines asIn VitroCytotoxic and Antimicrobial Candidates

Faidallah

Rostom

Khan

2016

Journal of Chemistry

Self Cite

View full text Add to dashboard Cite

show abstract

“…On the other hand, oxo‐tetrahydroindole molecules exhibited a broad spectrum of biological activities such as antibacterial, progesterone receptor agonist, CRTH 2 receptor antagonist, antimalerial, anti‐proliferative, MDM 2 ‐p53 interaction inhibitor and cytotoxic activity (Figure ). Therefore, synthesis of multi‐functionalized oxo‐tetrahydroindoles by MCRs can be considered as an important achievement .…”

Section: Introductionmentioning

confidence: 99%

Microwave Assisted One‐Pot Multicomponent Synthesis Using ZnO‐β Zeolite Nanoparticle: An Easy Access to 7‐Benzodioxolo[4,5‐b]xanthene‐dione and 4‐Oxo‐tetrahydroindole Scaffolds

Lambat¹,

Mahmood

Ledade

et al. 2020

ChemistrySelect

View full text Add to dashboard Cite

ZnO‐β zeolite nanoparticle has been introduced as, an inexpensive and efficient heterogeneous catalyst for the one‐pot multicomponent synthesis of 7‐benzodioxolo[4,5‐b]xanthenedione and 4‐oxo‐tetrahydroindole derivatives under microwave (MW) irradiations. The method offers several advantages such as excellent yields of the products (>90%), simple work‐up procedures, faster reactions, use of MW as source of energy and recyclability of the catalyst.

show abstract

Synthesis, Anti‐Inflammatory Activity, and COX‐1/2 Inhibition Profile of Some Novel Non‐Acidic Polysubstituted Pyrazoles and Pyrano[2,3‐c]pyrazoles

Faidallah

Rostom

2017

Archiv der Pharmazie

Self Cite

View full text Add to dashboard Cite

The synthesis and evaluation of the anti-inflammatory activity of some structure hybrids comprising basically the 5-hydroxy-3-methyl-1-phenyl-4-substituted-1H-pyrazole scaffold directly linked to a variety of heterocycles and functionalities, or annulated as pyrano[2,3-c]pyrazoles, is described. According to the in vivo results and a comprehensive structure-activity relationship study, five analogs (5, 10, 17, 19, and 27) displayed remarkable anti-inflammatory profiles showing distinctive % protection and ED values, especially 10 and 27 (ED 35.7 and 38.7 μmol/kg, respectively) which were nearly equiactive to celecoxib (ED 32.1 μmol/kg). Compounds 10, 17, and 27 exhibited distinctive COX-2 inhibition with a noticeable COX-2 selectivity (SI values 7.83, 6.87, and 7.16, respectively), close to that of celecoxib (SI 8.68). Additionally, 5, 10, 17, 19, and 27 proved to be gastrointestinal tract safe (0-20% ulceration) and non-toxic, being well tolerated by the experimental animals up to 250 mg/kg orally and 80 mg/kg parenterally. Collectively, the in vivo ED values for the most potent five derivatives agree with their in vitro COX-2 selectivity indices, suggesting their usefulness as selective anti-inflammatory COX-2 inhibitors. The bipyrazole 10 and the pyranopyrazole 27 could be considered as the most active members in this study, being nearly equiactive to celecoxib, besides their obvious selective COX-2 inhibition, high safety margin, and predicted pharmacokinetic (ADME-T) suitability for oral use.

show abstract

Synthesis and in vitro antitumor and antimicrobial activity of some 2,3-diaryl-7-methyl-4,5,6,7-tetrahydroindazole and 3,3a,4,5,6,7-hexahydroindazole derivatives

Cited by 17 publications

References 28 publications

Synthesis of Some Polysubstituted Nicotinonitriles and Derived Pyrido[2,3-d]pyrimidines asIn VitroCytotoxic and Antimicrobial Candidates

Synthesis of Some Polysubstituted Nicotinonitriles and Derived Pyrido[2,3-d]pyrimidines asIn VitroCytotoxic and Antimicrobial Candidates

Microwave Assisted One‐Pot Multicomponent Synthesis Using ZnO‐β Zeolite Nanoparticle: An Easy Access to 7‐Benzodioxolo[4,5‐b]xanthene‐dione and 4‐Oxo‐tetrahydroindole Scaffolds

Synthesis, Anti‐Inflammatory Activity, and COX‐1/2 Inhibition Profile of Some Novel Non‐Acidic Polysubstituted Pyrazoles and Pyrano[2,3‐c]pyrazoles

Contact Info

Product

Resources

About