17647-21-1Relevant articles and documents
Design, Synthesis, and Evaluation of Some Novel Heterocycles Bearing Pyrazole Moiety as Potential Anticancer Agents
Abdelgawad, Nancy,Ismail, Mahmoud F.,Hekal, Mohamed H.,Marzouk, Magda I.
, p. 1771 - 1779 (2019)
1,3-Diphenylpyrazole-4-carboxylaldehyde and o-hydroxyacetophenone were exploited as starting materials for the synthesis of novel substituted chalconated pyrazole derivative. The proclivity of this compound towards carbon and nitrogen nucleophiles such as malononitrile, diethyl malonate, ethyl cyanoacetate, ethyl acetoacetate, semicarbazide, thiosemicarbazide, and hydroxylamine has been investigated. The structures of all synthesized compounds were ascertained by analytical and spectral data. The antitumor activity of the target synthesized compounds was tested against a panel of two human tumor cell lines, namely, hepatocellular carcinoma (liver) HepG2 and mammary gland breast MCF-7.
H3PO4 catalyzed one-pot synthesis of 1,3-diphenyl-1H-pyrazole-4-carbaldehyde to novel 1,3-diphenyl-1H-pyrazole-4-carbonitrile
Choudhare, Tukaram S,Netankar, Prashant D,Shirsath, Sagar E,Wagare, Devendra S
, (2021/07/10)
Abstract: One-pot condensation of pyrazole-4-aldehydes and hydroxylamine hydrochloride to form the corresponding oxime using formic acid as a medium and further dehydration of oxime using a catalytic amount of orthophosphoric acid to afford novel pyrazole-4-carbonitrile. This protocol serves as an ortho-phosphoric acid-catalyzed one-pot conversion of aldehyde to nitrile. Most remarkable features of this method are metal-free, cost-effective, atom efficiency with excellent yield (98–99%). This process will serve as a robust and scalable tool for the synthesis of valuable and versatile precursor (nitriles). This precursor will pave the way for the synthesis of various medicinally important valuable compounds. Graphic abstract: [Figure not available: see fulltext.].
Microwave-assisted synthesis and biological evaluation of pyrazole-4-carbonitriles as antimicrobial agents
Kumar, Anil,Kumari, Poonam,Singh, Karan,Sood, Sumit,Yadav, Ajar Nath
, (2020/05/25)
An efficient microwave-assisted method of synthesis of pyrazole-4-carbonitriles has been developed. Condensation of pyrazole-4-carbaldehydes with hydroxylamine hydrochloride followed by reaction of the resulting oximes with the Vilsmeier-Haack reagent pre-formed from phthaloyl dichloride and dimethylformamide under microwave irradiation afforded the corresponding pyrazole-4-carbonitriles in 73percent to 91percent yield. The operational simplicity, avoidance of toxic reagents such as POCl3, shorter reaction time, higher yield compared to the classical version, easy work up, and the use of the by-product in the regeneration of phthaloyl dichloride are the advantages of this methodology. All the target compounds were tested for antimicrobial activity against Gram-positive bacteria Bacillus cereus and Staphylococcus aureus; Gram-negative bacteria Escherichia coli and Yersinia enterocolitica, and the fungal species Candida albicans.
Synthesis and antimicrobial evaluation of some heterocyclic compounds from 3-Aryl-1-phenyl-1H-pyrazole-4-carbaldehydes
Ramadan, El Sayed,Sharshira, Essam M.,El Sokkary, Ramadan I.,Morsy, Noussa
, p. 389 - 397 (2018/05/30)
A new series of chalcones, pyrazolinyl-pyrazoles, pyrazole-4-carbaldehyde oximes, pyrazole-4-carbonitriles, 5-pyrazolyl-1,2,4-Triazolidine-3-Thiones, and Knoevenagel condensation products was synthesized from 3-Aryl-1-phenyl-1H-pyrazole-4-carbaldehydes. Most reactions were carried out either without solvent or in the presence of water as a green solvent. The structure of synthesized compounds was characterized by spectral and elemental analysis. The synthesized compounds were tested in vitro for their antimicrobial activity against Escherichia coli, Staphylococcus aureus, and Candida albicans in comparison with imipenem (intravenous β-lactam antibiotic) and clotrimazole (antifungal medication) as reference drugs by using the agar diffusion technique. 3-Aryl-1-phenyl-1H-pyrazole-4-carbonitriles 8b, 8c, and 8d showed significant antifungal activity against the fungus C. albicans.
Design, synthesis, in Silico toxicity prediction, molecular docking, and evaluation of novel pyrazole derivatives as potential antiproliferative agents
Parameshwar, Ravula,Harinadha Babu, Vamaraju,Manichandrika, Paturi,Narendra Sharath Chandra,Swetha, Kolli
, p. 187 - 202 (2016/03/12)
A new series of pyrazole derivatives were designed by docking into vascular endothelial growth factor receptor-2 (VEGFR-2) kinase active site. The designed compounds were synthesized and evaluated for in vitro antiproliferative activity against HT-29 colo
Synthesis and biological evaluation of pyrazolylthiazole carboxylic acids as potent anti-inflammatory-antimicrobial agents
Khloya, Poonam,Kumar, Satish,Kaushik, Pawan,Surain, Parveen,Kaushik, Dhirender,Sharma, Pawan K.
, p. 1177 - 1181 (2015/03/14)
Current Letter presents design, synthesis and biological evaluation of a novel series of pyrazolylthiazole carboxylates 1a-1p and corresponding acid derivatives 2a-2p. All 32 novel compounds were tested for their in vivo anti-inflammatory activity by carrageenan-induced rat paw edema method as well as for in vitro antimicrobial activity. All the tested compounds exhibited excellent AI activity profile. Three compounds 1p (R = Cl, R1 = Cl), 2c (R = H, R1 = F) and 2n (R = Cl, R1 = OCH3) were identified as potent anti-inflammatory agents exhibiting edema inhibition of 93.06-89.59which is comparable to the reference drug indomethacin (91.32%) after 3 h of carrageenan injection while most of the other compounds displayed inhibition ≥80%. In addition, pyrazolylthiazole carboxylic acids (2a-2p) also showed good antimicrobial profile. Compound 2h (R = OCH3, R1 = Cl) showed excellent antimicrobial activity (MIC 6.25 μg/mL) against both Gram positive bacteria comparable with the reference drug ciprofloxacin (MIC 6.25 μg/mL).
Synthesis of novel pyrazolyl tetrazoles as selective COX-2 inhibitors
Swetha, Kolli Sri,Parameshwar, Ravula,Reddy, B. Madhava,Babu, V. Harinadha
, p. 4886 - 4892 (2013/09/23)
A series of novel pyrazolyl tetrazoles were synthesized by introducing tetrazole moiety at the fourth position of 1,3-substituted pyrazole nucleus. Synthesis was carried out by cyclization of different pyrazolonitriles using sodium azide in the presence of triethylammonium chloride as phase transfer catalyst. The structures of the synthesized compounds were confirmed on the basis of physical and spectral data. Among the synthesized compounds, 4b and 4e displayed significant anti-inflammatory activity with no observable ulcerogenic effect when compared with diclofenac sodium. Furthermore, compounds 4b and 4e were found to have COX-2 selectivity with a ratio of 0.44 and 0.48, respectively.
Synthesis and biological evaluation of some thiazolylpyrazole derivatives as dual anti-inflammatory antimicrobial agents
Bekhit, Adnan A.,Fahmy, Hesham T.Y.,Rostom, Sherif A.F.,Bekhit, Alaa El-Din A.
experimental part, p. 6027 - 6038 (2011/01/13)
The synthesis of a novel series of 4-thiazolylpyrazolyl derivatives is described in the present report. All the newly synthesized compounds were examined for their anti-inflammatory activity using cotton pellet-induced granuloma and carrageenan-induced rat paw edema bioassays. Their inhibitory activities of cyclooxygenase-1 and cyclooxygenase-2 (COX-1 and COX-2), ulcerogenic effect and acute toxicity were also determined. Furthermore, all compounds were evaluated for their in vitro antimicrobial activity against Escherichia coli, Staphylococcus aureus and Candida albicans. A docking pose for compounds 8b, 10a and 10b separately in the active site of the human COX-2 enzyme and DNA-gyrase B was also obtained. The results revealed that compounds 8b, 10a and 10b exhibited good anti-inflammatory activity with no or minimal ulcerogenic effect and good safety margin. Compounds 10a and 10b were found to be the most potent anti-inflammatory agents in the present study. Meanwhile, 10a and 10b displayed higher selective inhibitory activity towards COX-2 compared to indomethacin. Moreover, compounds 10a and 10b exhibited promising antibacterial against both E. coli and S. aureus. Docking studies for 8b, 10a and 10b with COX-2 (PDB ID: 1CX2) and DNA-gyrase B (PDB ID: 1EI1) showed good binding profile.
Synthesis and antibacterial activity of l, 3-diaryl-4-cyanopyrazoles
Prakash, Om,Pundeer, Rashmi,Ranjan, Pooja,Pannu, Kamaljeet,Dhingra, Yogita,Aneja
experimental part, p. 563 - 568 (2009/12/24)
A mild, short and simple method for the small scale synthesis of pharmaceutical important l, 3-diaryl-4- cyanopyrazoles 3 is reported from acetophenone arylhydrazones 1 through a two step reaction. All the title compounds have been subjected to in vitro a
