6332-22-5Relevant academic research and scientific papers
Crystal engineering with pyrazolyl-thiazole derivatives: Structure-directing role of π-stacking and σ-hole interactions
Ahmed, Muhammad Naeem,Madni, Murtaza,Anjum, Shaista,Andleeb, Saiqa,Hameed, Shahid,Khan, Abdul Majeed,Ashfaq, Muhammad,Tahir, Muhammad Nawaz,Gil, Diego M.,Frontera, Antonio
, p. 3276 - 3287 (2021/05/17)
The synthesis and X-ray characterization of 1-(2-(3-(4-bromophenyl)-5-(4-methoxyphenyl)-4,5-dihydro-1H-pyrazol-1-yl)-4-methylthiazol-5-yl)ethanone (7), ethyl 2-(5-(4-bromophenyl)-3-(4-chlorophenyl)-4,5-dihydropyrazol-1-yl)thiazole-4-carboxylate (8) and 2-(5-(4-chlorophenyl)-3-phenyl-4,5-dihydro-1H-pyrazol-1-yl)-N′-(2-hydroxy-3-methoxybenzylidene)thiazole-4-carbohydrazide (10) are described in this manuscript. The structure-directing role of a variety of noncovalent interactions has been analyzed energetically using DFT calculations and Hirshfeld surface analysis. Moreover, the existence and importance of halogen and chalcogen bonding interactions have been analyzed by using the quantum theory of atoms in molecules and the noncovalent interaction index (NCIplot).
Efficient base-free asymmetric one-pot synthesis of spiro[indoline-3,3′-pyrrolizin]-2-one derivatives catalyzed by chiral organocatalyst
Chithiraikumar, Chinnadurai,Ponmuthu, Kottala Vijaya,Harikrishnan, Muniyasamy,Malini, Nelson,Sepperumal, Murugesan,Siva, Ayyanar
, p. 895 - 909 (2020/10/29)
A 1,3-dipolar cycloaddition reaction has been performed under organocatalytic conditions with high enantioselectivity by the utilization of bipyridine-based chiral quaternary ammonium bromide as an organocatalyst. Here, the reaction of 1,3-dipolar cycloaddition of azomethine ylide generated in situ from the decarboxylative condensation of α-amino acids and non-enolizable 1,2-diketones to the above dipolarophiles takes place.
Transition metal-free domino aryl-aryl coupling/phospha-Michael addition of diarylphosphinite to α,β-unsaturated ketones triggered by alkaline hydrolysis of (4-(2-alkenoyl)phenyl)triarylphosphonium salts
Huang, Wenhua,Xue, Jing-Yu
, (2021/11/08)
Alkaline hydrolysis of a variety of (4-(2-alkenoyl)phenyl)triarylphosphonium bromides is reported. This hydrolysis triggers coupling of 4-(2-alkenoyl)phenyl with one aryl via phosphorus(V). Both diarylphosphinite and an α,β-unsaturated ketone are in situ generated and then undergo phospha-Michael addition to provide β-diarylphosphoryl ketones bearing a biaryl moiety in 27–70% yields in the absence of a transition metal.
Lewis acid catalyst system for Claisen-Schmidt reaction under solvent free condition
Halpani, Chandni G.,Mishra, Satyendra
, (2020/07/16)
Ca(OTf)2 in combination with NBu4.BF4 was established to function as an efficient catalyst system for one-pot Claisen-Schmidt condensation under neat conditions. Substituted acetophenones and benzaldehydes were coupled in situ to afford their corresponding chalcones in excellent yields. The method, with a broad range of substrate tolerance and mild operational conditions can produce assorted chalcone derivatives in moderate to high yields from easily accessible starting materials.
Microwave-irradiated synthesis and biological evaluation of 3,5-diaryl-1-phenyl-2-pyrazolines as antibacterial and anti-inflammatory agents
Kumar, Anjan,Rout, Sradhasini,Panda, Jnyanaranjan,Sahoo, Biswa Mohan,Banik, Bimal Krishna
, p. 1321 - 1326 (2020/06/27)
In a wide search program towards a biologically active antibacterial and anti-inflammatory agents, a series of 3,5-diaryl-1-phenyl-2-pyrazoline have been synthesized with excellent yields employing microwave techniques starting from substituted α,β-unsaturated carbonyl compounds which undergo cyclization reactions with phenylhydrazine. The structures of newly synthesized compounds were characterized and confirmed on the basis of FT-IR, 1H NMR and mass spectral analyses. The synthesized compounds 3,5-diaryl-1-phenyl-2-pyrazolines had shown significant activity against Staphylococcus aureus (MTCC 87), Escherichia coli (MTCC 40), Pseudomonas aeruginosa (MTCC 424) and Proteus vulgaris (MTCC 426) by cup plate method using tetracycline-SD 037 as a reference standard. The anti-inflammatory property of 1,3,5-diaryl-1-phenyl-2-pyrazolines were screened by using carragenan induced paw edema method in Wistar rat. The anti-inflammatory activities were comparable to that of the standard drug diclofenac. The safety of 3,5-diaryl-1-phenyl-2-pyrazolines were reflected by toxicity studies.
Synthesis, spectroscopic characterization, and computed optical analysis of green fluorescent cyclohexenone derivatives
Nazar, Muhammad Faizan,Badshah, Amir,Mahmood, Asif,Zafar, Muhammad Naveed,Janjua, Muhammad Ramzan Saeed Ashraf,Raza, Muhammad Asam,Hussain, Riaz
, p. 152 - 160 (2016/03/08)
Cyclohexenone containing chalcones core is one important class of materials, which exhibit high nonlinear optical (NLO) responses and good crystallizability. The present study reports the successful development of six new fluorescent cyclohexenone derivat
Facile Microwave-assisted Synthesis of 1,3,5-Trisubstituted Pyrazoline Derivatives Incorporating Sulfonyl Moiety
Liu, Fei,Yang, Jin-Feng,Liu, Hong,Wei, Wen-Zhen,Ma, Yan-Mei
, p. 254 - 260 (2016/04/19)
We developed an environmentally benign, convenient microwave-assisted process for the construction of 1,3,5-trisubstitued pyrazolines (10a～10f, 11a～11f, 12a～12f, 13a～13f). Chalcones, as the key intermedi- ates, were obtained by the condensation of each of appropriately substituted aromatic aldehydes (1～4) with 4-substituted acetophenones (5a～5f) via a Claisen-Schmidt reaction under the action of microwave irradiation. Cyclization of the chalcones (6a～6f, 7a～7f, 8a～8f, 9a～9f) with p-toluene sulfonhydrazide af- forded 1,3,5-trisubstitued pyrazoline derivatives using microwave-assisted process in 25 min and 140 watt power in glycol. The structures of targeted compounds were established by IR, 1H NMR, MS and ele- mental analysis. The results indicate that microwave-assisted synthetic process presents advantages in terms of enhancement in rate, decrease in reaction time, clean reaction and convenient operation.
Synthesis, anti-inflammatory, analgesic, COX-1/2 inhibition activities and molecular docking study of pyrazoline derivatives
Abdel-Sayed, Maged A.,Bayomi, Said M.,El-Sherbeny, Magda A.,Abdel-Aziz, Naglaa I.,Eltahir, Kamal Eldin H.,Shehatou, George S.G.,Abdel-Aziz, Alaa A.-M.
, p. 2032 - 2042 (2016/04/20)
Design, synthesis and pharmacological activities of a group of 1,3,5-trisubstituted pyrazolines were reported. The chemical structures of the synthesized compounds have been assigned on the basis of IR, MS, 1H NMR, and 13C NMR spectral analyses. The synthesized 1,3,5-trisubstituted pyrazoline derivatives were evaluated in vivo for anti-inflammatory, analgesic activities and in vitro for COX-1/2 inhibition assay. Among the tested compounds, derivatives 4h, 6e, 7a, 7e, and 9 showed more potent anti-inflammatory and analgesic activities than the reference drug celecoxib. On the basis of their higher activities in the in vivo studies compared with celecoxib, the five compounds 4h, 6e, 7a, 7e and 9 were selected to test their inhibitory activities against ovine COX-1/2 using an in vitro cyclooxygenase inhibition assay. Docking study of compounds 7a, 7e and 9 into the COX-2 binding site revealed a similar binding mode to SC-558, a selective COX-2 inhibitor.
Novel benzothiazole based sulfonylureas/sulfonylthioureas: Design, synthesis and evaluation of their antidiabetic potential
Kharbanda, Chetna,Alam, Mohammad Sarwar,Hamid, Hinna,Javed, Kalim,Bano, Sameena,Ali, Yakub,Dhulap, Abhijeet,Alam, Parwez,Pasha
, p. 6777 - 6786 (2016/08/10)
In the present study, twenty-eight benzothiazole based sulfonylureas/sulfonylthioureas were synthesized and were assessed for their antidiabetic effect in a normoglycemic rat model by the in vivo oral glucose tolerance test (OGTT). All the synthesized com
Antimycobacterial and anti-inflammatory activities of substituted chalcones focusing on an anti-tuberculosis dual treatment approach
Ventura, Thatiana Lopes Biá,Calixto, Sanderson Dias,De Azevedo Abrahim-Vieira, Bárbara,De Souza, Alessandra Mendon?a Teles,Mello, Marcos Vinícius Palmeira,Rodrigues, Carlos Rangel,De Mariz E Miranda, Leandro Soter,De Souza, Rodrigo Octavio Mendon?a Alves,Leal, Ivana Correa Ramos,Lasunskaia, Elena B.,Muzitano, Michelle Fraz?o
, p. 8072 - 8093 (2015/05/20)
Tuberculosis (TB) remains a serious public health problem aggravated by the emergence of M. tuberculosis (Mtb) strains resistant to multiple drugs (MDR). Delay in TB treatment, common in the MDR-TB cases, can lead to deleterious life-threatening inflammation in susceptible hyper-reactive individuals, encouraging the discovery of new anti-Mtb drugs and the use of adjunctive therapy based on anti-inflammatory interventions. In this study, a series of forty synthetic chalcones was evaluated in vitro for their anti-inflammatory and antimycobacterial properties and in silico for pharmacokinetic parameters. Seven compounds strongly inhibited NO and PGE2 production by LPS-stimulated macrophages through the specific inhibition of iNOS and COX-2 expression, respectively, with compounds 4 and 5 standing out in this respect. Four of the seven most active compounds were able to inhibit production of TNF-α and IL-1β. Chalcones that were not toxic to cultured macrophages were tested for antimycobacterial activity. Eight compounds were able to inhibit growth of the M. bovis BCG and Mtb H37Rv strains in bacterial cultures and in infected macrophages. Four of them, including compounds 4 and 5, were active against a hypervirulent clinical Mtb isolate as well. In silico analysis of ADMET properties showed that the evaluated chalcones displayed satisfactory pharmacokinetic parameters. In conclusion, the obtained data demonstrate that at least two of the studied chalcones, compounds 4 and 5, are promising antimycobacterial and anti-inflammatory agents, especially focusing on an anti-tuberculosis dual treatment approach.
