Synthesis of some novel pyridine and naphthyridine derivatives

Abdelrazek, Fathy M.; Kassab, Nazmi A.; Metwally, Nadia H.; Sobhy, Nehal A.

doi:10.5155/eurjchem.1.4.368-372.104

Cited by 10 publications

(5 citation statements)

References 24 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Next, the reactivity of thiosemicarbazone derivative 2 towards hydrazonoyl halide, be bereft of a-keto group, was examined. In the present study, we have established that reaction of ethylidenethiosemicarbazone 2 with N-phenylcarbohydrazonoyl chloride (14) gave the 1,3,4-thiadiazole 17 as the end product (Scheme 2). The reaction proceeded via S-alkylation, 22 with removal of hydrogen chloride, to give S-alkylated intermediates 15 followed by intramolecular Michael 23…”

Section: Scheme 1 Synthesis Of the Arylazothiazoles 5a-h And 9a-dmentioning

confidence: 70%

“…10,11 In the last two decades we have been involved in a program aiming at the synthesis of functionally substituted heterocyclic compounds from cheap laboratory available starting materials with anticipated biological activities. [12][13][14][15][16][17][18][19][20] Recently, in the frame of our program, some new functionally substituted thiazoles and / or bisthiazoles were required to be screened for their biological activity as antitumor agents. It seemed to us that the combination of a thiazole ring with a pyridine ring in one entity may lead to enhanced biological activity due to the synergistic effect of both rings.…”

mentioning

confidence: 99%

See 1 more Smart Citation

Synthesis of Some Novel Thiazole, Thiadiazole and 1,4-Phenylene-bis-thiazole Derivatives as Potent Antitumor Agents

Gomha¹,

Abdelrazek²,

Abdelrahman³

et al. 2016

HETEROCYCLES

View full text Add to dashboard Cite

A novel series of 2-ethylidenehydrazono-5-arylazothiazoles 5a-h and 2-ethylidenehydrazono-5-arylazothiazolones 9a-d were prepared by cyclocondensation of hydrazonyl halides 3a-h and 7a-d with ethylidenethiosemicarbazide 2. In addition, reaction of 2 with N-phenylcarbohydrazonyl chloride (14), afforded 1,3,4-thiadiazole derivative 17 as the end product. Moreover, the thiosemicarbazide derivative 2 was reacted with various bromoacetyl compounds 19a-d and 1,1'-(1,4-phenylene)bis(2-bromoethanone) (21) furnished the respective thiazole derivatives 20a-d and 1,4-phenylene-bisthiazole derivative 22. The structures of the newly synthesized compounds were established on the basis of spectroscopic evidences and their alternative syntheses. The newly synthesized compounds were evaluated for their antitumor activities against hepatocellular carcinoma (HepG2) cell line and the results revealed promising activities of compounds 5h, 5d, 5g, 5f and 5e with IC50 equal 2.23 ± 0.28, 2.48 ± 0.34, 2.49 ± 0.24, 4.03 ± 0.11, and 5.32 ± 0.27 μM, respectively. Functionalized thiazole derivatives have received much attention due to their diverse biological activities such as antimicrobial, 1 antiviral, 2 cytotoxic and antitumor, 3-6 and HIV-protease inhibitory agents. 7 Compounds incorporating two thiazole rings either directly connected as in bisthiazoles or through a linker unit as in bisthiazolyl compounds, show pronounced biological activity as DNA replication inhibitors in the tumor cells 8 and HIV-protease inhibitors. 7-9 Pyridine deivatives also play a key role catalyzing both biological and chemical systems. In many enzymes of living organisms it is the prosthetic pyridine nucleotide (NADP) that is involved in various 954

show abstract

Section: Scheme 1 Synthesis Of the Arylazothiazoles 5a-h And 9a-dmentioning

confidence: 70%

mentioning

confidence: 99%

Synthesis of Some Novel Thiazole, Thiadiazole and 1,4-Phenylene-bis-thiazole Derivatives as Potent Antitumor Agents

Gomha¹,

Abdelrazek²,

Abdelrahman³

et al. 2016

HETEROCYCLES

View full text Add to dashboard Cite

show abstract

“…Naphthyridine derivatives have been reported as antifungal 21 , anticancer 22 , antibacterial 23 , GSK-3 inhibitors 24 , trypanocidal 25 , insecticidal 26 acetyl and butyryl-cholinestrase inhibitors 27 , 28 . Their anticancer effect was previously studied by various research groups.…”

Section: Introductionmentioning

confidence: 99%

Pyrazole derivatives of pyridine and naphthyridine as proapoptotic agents in cervical and breast cancer cells

Alharthy

Rashid

Ashraf

et al. 2023

Sci Rep

View full text Add to dashboard Cite

Cancer is one of the leading causes of death worldwide. The increasing prevalence and resistance to chemotherapy is responsible for driving the search of novel molecules to combat this disease. In search of novel compounds with pro-apoptotic potential, pyrazolo-pyridine and pyrazolo-naphthyridine derivatives were investigated against cervical cancer (HeLa) and breast cancer (MCF-7) cells. The anti-proliferative activity was determined through the MTT assay. Potent compounds were then analyzed for their cytotoxic and apoptotic activity through a lactate dehydrogenase assay and fluorescence microscopy after propidium iodide and DAPI staining. Flow cytometry was used to determine cell cycle arrest in treated cells and pro-apoptotic effect was verified through measurement of mitochondrial membrane potential and activation of caspases. Compounds 5j and 5k were found to be most active against HeLa and MCF-7 cells, respectively. G0/G1 cell cycle arrest was observed in treated cancer cells. Morphological features of apoptosis were also confirmed, and an increased oxidative stress indicated the involvement of reactive oxygen species in apoptosis. The compound-DNA interaction studies demonstrated an intercalative mode of binding and the comet assay confirmed the DNA damaging effects. Finally, potent compounds demonstrated a decrease in mitochondrial membrane potential and increased levels of activated caspase-9 and -3/7 confirmed the induction of apoptosis in treated HeLa and MCF-7 cells. The present work concludes that the active compounds 5j and 5k may be used as lead candidates for the development of lead drug molecules against cervical and breast cancer.

show abstract

“…In these last two decades, we have launched a program designed to create new easy, synthetic paths to heterocyclic systems that are functionally replaced, using inexpensive laboratory materials with anticipated bioactivities . Under our program, some new pyridine‐fused aza heterocyclic compounds have to be evaluated for biological activity.…”

Section: Introductionmentioning

confidence: 99%

“…[29][30][31] In these last two decades, we have launched a program designed to create new easy, synthetic paths to heterocyclic systems that are functionally replaced, using inexpensive laboratory materials with anticipated bioactivities. [32][33][34][35][36][37][38][39][40][41][42] Under our program, some new pyridine-fused aza heterocyclic compounds have to be evaluated for biological activity. It was expected that combining a triazole ring with a pyridine and/or a pyrimidine ring in one system could lead to improved biological activity.…”

Section: Introductionmentioning

confidence: 99%

Efficient synthesis and In Silico study of some novel pyrido[2,3‐d][1,2,4]triazolo[4,3‐a]pyrimidine derivatives

Abdelrazek

Gomha

Abdel‐aziz

et al. 2020

Journal of Heterocyclic Chem

View full text Add to dashboard Cite

A novel series of 1,5‐dihydropyrido‐triazolo‐pyrimidine derivatives were prepared by cyclocondensation of 2‐thioxo‐pyrido[2,3‐d]pyrimidines (prepared from reaction of chalcone with 6‐aminothiouracil) with a variety of hydrazonoyl chlorides. Based on spectroscopic evidence and their chemical syntheses, the structures of the newly prepared compounds were elucidated. Designated compounds are forced for molecular docking by using MOE 2014.010 Package software; one of in silico study tools. Synthesized compounds are targeting Human Cyclin‐defendant Kinase 2 (CK2) PDB ID (1PXO.Protein data bank) due to its important role in controlling the human cell cycle and also for meiosis.

show abstract

Synthesis of some novel pyridine and naphthyridine derivatives

Cited by 10 publications

References 24 publications

Synthesis of Some Novel Thiazole, Thiadiazole and 1,4-Phenylene-bis-thiazole Derivatives as Potent Antitumor Agents

Synthesis of Some Novel Thiazole, Thiadiazole and 1,4-Phenylene-bis-thiazole Derivatives as Potent Antitumor Agents

Pyrazole derivatives of pyridine and naphthyridine as proapoptotic agents in cervical and breast cancer cells

Efficient synthesis and In Silico study of some novel pyrido[2,3‐d][1,2,4]triazolo[4,3‐a]pyrimidine derivatives

Contact Info

Product

Resources

About