Novel Ester and Acid Derivatives of the 1,5-Diarylpyrrole Scaffold as Anti-Inflammatory and Analgesic Agents. Synthesis and in Vitro and in Vivo Biological Evaluation

Abstract(E)-N’-Benzylidene-7-methyl-2-propyl-1H-benzo [d]imidazole-5-carbohydrazides (5a-r) have been synthesized from 7-methyl-2-propyl-1H-benzo[d]imidazole-5-carbohydrazide (3) by condensing with different aromatic aldehydes (4a-r). Title compounds (5a-r) were evaluated for in vitro antioxidant activity and based on their potential for antioxidant property, selected compounds 5d and 5m-p were screened for in vivo anti-inflammatory and analgesic activity. The results indicate that the compound 5o and 5p are effective against anti-inflammatory and analgesic activity. The biological data was further supported by molecular docking studies, which revealed the binding pattern and the affinity of the molecules in the active site of COX-2.

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Synthesis and biological evaluation of some novel pyrazolopyrimidines incorporating a benzothiazole ring system

Acta Pharmaceutica ◽

10.2478/acph-2013-0001 ◽

2013 ◽

Vol 63 (1) ◽

pp. 19-30 ◽

Cited By ~ 11

Author(s):

Mohammed Afzal Azam ◽

Loganathan Dharanya ◽

Charu Chandrakant Mehta ◽

Sumit Sachdeva

Keyword(s):

Antimicrobial Activity ◽

Diclofenac Sodium ◽

Biological Evaluation ◽

Ring System ◽

Standard Drug ◽

Anti Inflammatory ◽

Pyrimidine Moiety ◽

Synthesis And Biological Evaluation

In the present study, a series of benzothiazol derivatives 3a-l containing pyrazolo[3,4-d]pyrimidine moiety at the second position were synthesized and characterized by analytical and spectral data. The compounds were tested for their in vitro antimicrobial activity. Compounds 1-(1,3-benzothiazol-2- yl)-3-methyl-4-phenyl-1H-pyrazolo[3,4-d]pyrimidine (3a), 1- (1,3-benzothiazol-2-yl)-4-(4-chlorophenyl)-3-methyl-1H-pyrazolo[ 3,4-d]pyrimidine (3d) and 1-(1,3-benzothiazol-2-yl)- 3-methyl-4-substituted phenyl-1H-pyrazolo[3,4-d]pyrimidines (3h-j) showed significant inhibitory activity against P. aeruginosa whereas compounds 1-(1,3-benzothiazol-2-yl)-4- (2-chlorophenyl)-3-methyl-1H-pyrazolo[3,4-d]pyrimidine (3b), 2-[1-(1,3-benzothiazol-2-yl)-3-methyl-1H-pyrazolo[3,4-d]pyrimidin- 4-yl]phenol (3e), 1-(1,3-benzothiazol-2-yl)-4-(3,4-dimethoxyphenyl)- 3-methyl-1H-pyrazolo[3,4-d]pyrimidine (3h), 4-[1-(1,3-benzothiazol-2-yl)-3-methyl-1H-pyrazolo[3,4-d]pyri midin-4-yl]-N,N-dimethylaniline (3j) and 1-(1,3-benzothiazol- 2-yl)-3-methyl-4-[2-phenylvinyl]-1H-pyrazolo[3,4-d]pyrimidine (3k) were found to be active against C. albicans. Some of these synthesized compounds were evaluated for their in vivo acute toxicity, analgesic, anti-inflammatory, and ulcerogenic actions. The tested compound 4-[1-(1,3-benzothiazol- 2-yl)-3-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl]-N, N-dimethylaniline (3j) exhibited maximum analgesic and anti-inflammatory activities. Compounds 1-(1,3-benzothiazol- -2-yl)-3-methyl-4-(3-nitrophenyl)-1H-pyrazolo[3,4-d]pyrimidine (3i) and 3j showed a significant gastrointestinal protection compared to the standard drug diclofenac sodium.

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Synthesis, characterization and in vitro and in vivo anticancer activity of Pt(iv) derivatives of [Pt(1S,2S-DACH)(5,6-dimethyl-1,10-phenanthroline)]

Dalton Transactions ◽

10.1039/c7dt01054k ◽

2017 ◽

Vol 46 (21) ◽

pp. 7005-7019 ◽

Cited By ~ 25

Author(s):

Benjamin W. J. Harper ◽

Emanuele Petruzzella ◽

Roman Sirota ◽

Fernanda Fabiola Faccioli ◽

Janice R. Aldrich-Wright ◽

...

Keyword(s):

Anticancer Activity ◽

Biological Evaluation ◽

Synthesis And Biological Evaluation ◽

Derivatives Of

Synthesis and biological evaluation in vitro and in vivo of functionalized Pt(iv) derivatives of Pt56MeSS.

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Design, Synthesis and Biological Evaluation of Novel 1, 3, 4-Oxadiazole Bearing Pyridine Moiety

International Journal of Scientific Research in Science and Technology ◽

10.32628/ijsrst196535 ◽

2019 ◽

pp. 300-307

Author(s):

Asma D. Ambekari ◽

Shrinivas K. Mohite

Keyword(s):

Antimicrobial Activity ◽

Mass Spectra ◽

Biological Evaluation ◽

Design Synthesis ◽

Pyridine Moiety ◽

Anti Inflammatory ◽

Physicochemical Data ◽

Synthesis And Biological Evaluation

Series of novel substituted Synthesis of N-{[5-(substituted)-1,3,4-oxadiazole-2-yl] carbamothioyl} derivatives containing 1,3,4-oxadiazole moiety were synthesized by microwave as a green chemistry method and conventional method by using pyridine 3- carboxylic acid as a starting material. The structures of the synthesized compounds were characterized by physicochemical data, IR, Mass spectra and 1HNMR. All the newly synthesized compound screened for their antimicrobial and In-vivo and In-vitro Anti-inflammatory studies. Anti-inflammatory studies revealed that compound 4f showed significant in-vivo and in-vitro anti-inflammatory activity as well potent antimicrobial activity.

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Synthesis of new ibuprofen hybrid conjugates as potential anti-inflammatory and analgesic agents

Future Medicinal Chemistry ◽

10.4155/fmc-2020-0109 ◽

2020 ◽

Vol 12 (15) ◽

pp. 1369-1386

Author(s):

Siva S Panda ◽

Adel S Girgis ◽

Hitesh H Honkanadavar ◽

Riham F George ◽

Aladdin M Srour

Keyword(s):

Writhing Test ◽

Rat Paw Edema ◽

Analgesic Agents ◽

Inflammatory Drugs ◽

Cox 2 ◽

Anti Inflammatory ◽

Rat Paw ◽

Inhibition Studies

Background: A new set of hybrid conjugates derived from 2-(4-isobutylphenyl)propanoic acid (ibuprofen) is synthesized to overcome the drawbacks of the current non-steroidal anti-inflammatory drugs. Results & methodology: Synthesized conjugates were screened for their anti-inflammatory, analgesic and ulcerogenic properties. Few conjugates were found to have significant anti-inflammatory properties in the carrageenan-induced rat paw edema test, while a fair number of conjugates showed promising peripheral analgesic activity in the acetic acid-induced writhing test as well as central analgesic properties in the in vivo hot plate technique. The newly synthesized conjugates did not display any ulcerogenic liability. Conclusion: In vitro, COX-1 and COX-2 enzyme inhibition studies raveled compound 7e is more selective toward COX-2 compared with ibuprofen.

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Nitric oxide-donating derivatives of hederacolchiside A 1 : Synthesis and biological evaluation in vitro and in vivo as potential anticancer agents

Bioorganic & Medicinal Chemistry Letters ◽

10.1016/j.bmcl.2016.11.021 ◽

2017 ◽

Vol 27 (1) ◽

pp. 98-101 ◽

Cited By ~ 11

Author(s):

Yuanying Fang ◽

Rikang Wang ◽

Mingzhen He ◽

Hesong Huang ◽

Qi Wang ◽

...

Keyword(s):

Nitric Oxide ◽

Anticancer Agents ◽

Biological Evaluation ◽

Synthesis And Biological Evaluation ◽

Derivatives Of

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Synthesis of novel thiadiazole derivatives as selective COX-2 inhibitors

MedChemComm ◽

10.1039/c6md00367b ◽

2016 ◽

Vol 7 (12) ◽

pp. 2309-2327 ◽

Cited By ~ 10

Author(s):

Fatma A. Ragab ◽

Helmi I. Heiba ◽

Marwa G. El-Gazzar ◽

Sahar M. Abou-Seri ◽

Walaa A. El-Sabbagh ◽

...

Keyword(s):

Paw Oedema ◽

Analgesic Agents ◽

Thiadiazole Derivatives ◽

Cox 2 ◽

Anti Inflammatory ◽

Rat Paw ◽

Cox 2 Inhibitors ◽

Rat Paw Oedema

A novel series of thiadiazole derivatives were designed and synthesized for evaluation as selective COX-2 inhibitors in vitro and were investigated in vivo as anti-inflammatory and analgesic agents against carrageenan-induced rat paw oedema model in irradiated rats.

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Synthesis and Biological Evaluation of Some Pyrazole Derivatives, Containing (Thio) Semicarbazide, as Dual Anti-Inflammatory Antimicrobial Agents

Letters in Drug Design & Discovery ◽

10.2174/1570180816666190325163117 ◽

2019 ◽

Vol 16 (9) ◽

pp. 1020-1030

Author(s):

Zhaochang Liang ◽

Yuping Huang ◽

Shiben Wang ◽

Xianqing Deng

Keyword(s):

Antiinflammatory Activity ◽

Antimicrobial Activities ◽

Biological Evaluation ◽

Dilution Method ◽

Pyrazole Derivatives ◽

Reference Drug ◽

Tnf Α ◽

Anti Inflammatory

Background: Several series of pyrazole derivatives containing (thio) semicarbazide (4a-4h, 5a-5l, 6a-6f, 7a-7c) were designed and synthesized to screen dual inflammatory and antimicrobial activities. Methods: The products were characterized by1H NMR, 13C NMR and HRMS. In vitro LPS-induced TNF-α model and in vivo xylene-induced ear-edema model were used to evaluate their antiinflammatory activity. Their in vitro antimicrobial activities were evaluated using a serial dilution method against several gram-positive strains, gram-negative strains and a fungi strain. Results: Bioassays indicated that most of the compounds markedly inhibited the expression of TNF- α at the concentration of 20 µg/mL Compounds 5i, 6b, and 7b had comparable in vivo antiinflammatory activity to the reference drug dexamethasone at the dose of 50 mg/kg. In addition, several compounds showed antimicrobial activity against different strains, and compounds 5g and 5h exhibited potent inhibitory activities with the MIC value of 8 µg/mL against the Streptococcus pneumoniae CMCC 31968 and Staphylococcus aureus CMCC 25923, respectively. Compound 7b, which exhibited both anti-inflammatory and antimicrobial activities, should be studied as it is or after derivatization. Conclusion: It can be concluded that pyrazoles, with (thio)-semicarbazone moieties, have the potential to be developed into new anti-inflammatory agents.

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Synthesis and Biological Evaluation of Polyfluoroalkylated Antipyrines and their Isomeric O-Methylpyrazoles

Medicinal Chemistry ◽

10.2174/1573406414666181106145435 ◽

2019 ◽

Vol 15 (5) ◽

pp. 521-536 ◽

Cited By ~ 6

Author(s):

Natalya Agafonova ◽

Evgeny Shchegolkov ◽

Yanina Burgart ◽

Victor Saloutin ◽

Alexandra Trefilova ◽

...

Keyword(s):

Biological Activities ◽

Biological Evaluation ◽

Antipyretic Activity ◽

Starting Point ◽

Anti Inflammatory ◽

Analgesic Activities ◽

Synthesis And Biological Evaluation ◽

Cox 1

Background: Formally belonging to the non-steroidal anti-inflammatory drug class pyrazolones have long been used in medical practices. Objective: Our goal is to synthesize N-methylated 1-aryl-3-polyfluoroalkylpyrazolones as fluorinated analogs of antipyrine, their isomeric O-methylated derivatives resembling celecoxib structure and evaluate biological activities of obtained compounds. Methods: In vitro (permeability) and in vivo (anti-inflammatory and analgesic activities, acute toxicity, hyperalgesia, antipyretic activity, “open field” test) experiments. To suggest the mechanism of biological activity, molecular docking of the synthesized compounds was carried out into the tyrosine site of COX-1/2. Conclusion: The trifluoromethyl antipyrine represents a valuable starting point in design of the lead series for discovery new antipyretic analgesics with anti-inflammatory properties.

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