2443-68-7Relevant academic research and scientific papers
Synthesis of some hippuric acid substrate linked novel pyrazoles as antimicrobial agents
Verma, Anil,Kumar, Vinod,Khare, Rajshree,Singh, Joginder
, p. 522 - 526 (2019/02/06)
Escalating resistance of microorganisms to the currently accessible antimicrobial drugs has forced to synthesize some novel biologically active compounds as efficient alternates via economical substrates. Hence, hippuric acid was used as one of the starting materials to synthesize pyrazole derivatives. All the synthesized compounds were characterized by IR, NMR (1H & 13C) and mass spectral data. The antimicrobial potential of synthesized compounds has been explored against four bacterial and two fungal strains. Among the 12 compounds, 3 compounds 8j, 8k and 8l were found to exhibit prominent antimicrobial potential as compared with the standards ciprofloxacin and amphotericin-B.
Synthesis and docking studies of N-(5-(alkylthio)-1,3,4-oxadiazol-2-yl)methyl)benzamide analogues as potential alkaline phosphatase inhibitors
Iqbal, Zafar,Iqbal, Ambreen,Ashraf, Zaman,Latif, Muhammad,Hassan, Mubashir,Nadeem, Humaira
, p. 646 - 654 (2019/05/08)
A series of N-(5-(alkylthio)-1,3,4-oxadiazol-2-yl)methyl)benzamides 6a–i were synthesized as alkaline phosphatase inhibitors. The intermediate 5-substituted 1,3,4-oxadiazole-2-thione 4 was synthesized starting with hippuric acid. Hippuric acid in the first step was converted into corresponding methyl ester 2 which upon reaction with hydrazine hydrate furnished the formation of hydrazide 3. The hippuric acid hydrazide was then cyclized into 5-substituted 1,3,4-oxadiazole-2-thione 4. The intermediate 4 was then reacted with alkyl or aryl halides 5a–5i to afford the title compounds N-(5-(methylthio)-1,3,4-oxadiazol-2-yl)methyl)benzamides 6a–i. The bioassay results showed that compounds 6a–i exhibited good to excellent alkaline phosphatase inhibitory activity. The most potent activity was exhibited by the compound 6i having IC50 value 0.420 μM, whereas IC50 value of standard (KH2PO4) was 2.80 μM. Molecular docking studies was performed against alkaline phosphatase enzyme (PDBID 1EW2) to check binding affinity of the synthesized compounds 6a–i against target protein. The docking results showed that three compounds 6c, 6e, and 6i have maximum binding interactions with binding energy values of ?8 kcal/mol. The compound 6i displayed the interactions of oxadiazole ring nitrogen with amino acid His265 having a binding distance 2.13 ?. It was concluded from our results that synthesized compounds, especially compound 6i may serve as lead structure to design more potent inhibitors of human alkaline phosphatase.
Synthesis of Hydrazones from Amino Acids and their Antimicrobial and Cytotoxic Activities
Abid, Obaid-Ur-Rahman,Khatoon, Ghamama,Arfan, Muhammad,Sajid, Imran,Langer, Peter,Rehman, Wajid,Rahim, Fazal,Yasir, Muhammad,Waqar, Muhammad,Haleem, Kashif Syed
, p. 1079 - 1087 (2017/09/26)
Hydrazones 6a–6n were synthesized from different amino acids with various aldehydes under reflux in methanol/ethanol. The structures of synthesized compounds were ascertained by elemental analysis and spectroscopic techniques. A comparative study of the antimicrobial activity and cytotoxicity was carried out of the N-protected amino acids, their esters, hydrazides, and the respective hydrazones, providing good results in cytotoxicity studies.
2-azetidinone derivatives: Synthesis, antimicrobial, anticancer evaluation and QSAR studies
Deep, Aakash,Kumar, Pradeep,Narasimhan, Balasubramanian,Lim, Siong Meng,Ramasamy, Kalavathy,Mishra, Rakesh Kumar,Mani, Vasudevan
, p. 65 - 78 (2016/03/19)
A series of 2-azetidinone derivatives was synthesized from hippuric acid and evaluated for its in vitro antimicrobial and anticancer activities. Antimicrobial properties of the title compounds were investigated against Gram positive and Gram negative bact
4-Thiazolidinone derivatives: Synthesis, antimicrobial, anticancer evaluation and QSAR studies
Deep, Aakash,Narasimhan, Balasubrmanian,Lim, Siong Meng,Ramasamy, Kalavathy,Mishra, Rakesh Kumar,Mani, Vasudevan
, p. 109485 - 109494 (2016/11/30)
A series of 4-thiazolidinone derivatives (1-18) was synthesized and tested in vitro for its antimicrobial and anticancer potential. Synthesized compounds were found to be 5 more potent antimicrobial agents than anticancer agents. Anticancer screening resu
Synthesis, antimicrobial, anticancer evaluation and QSAR studies of thiazolidin-4-one derivatives
Deep, Aakash,Kumar, Pradeep,Narasimhan, Balasubrmanian,Ramasamy, Kalavathy,Lim, Siong Meng,Mani, Vasudevan,Mishra, Rakesh Kumar
, p. 93 - 106 (2016/03/19)
In this study, a novel series of 4-thiazolidinone derivatives (1-17) was synthesized and evaluated for its in vitro antimicrobial and anticancer potentials. N-(2-(5-(4-nitrobenzylidene)-2-(4-chlorophenyl)-4-oxothiazolidin- 3-ylamino)-2-oxoethyl) benzamide
Dibenzo-azepine-dione anti-tumor compounds and preparation method thereof
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, (2016/10/07)
The invention provides dibenzo-azepine-dione anti-tumor compounds and a preparation method thereof, belongs to the technical field of medicines and particularly relates to compounds with specific chemical structures with anti-tumor activity. General formulae of the compounds include a general formula I, a general formula II, a general formula III and a general formula IV. The invention further provides an application of the compounds in anti-tumor and the preparation method. Tests of various tumor cell lines such as human lung cancer cells and human gastric carcinoma cells prove that the compounds have the tumor activity inhibition effect. The raw materials of the compounds are easily available, the preparation method is simple, and experiments prove that the compounds have good anti-cancer effect and have good application prospect in the field of design, research and development of anti-tumor drugs.
Microwave assisted synthesis and docking study of N-(2-oxo-2-(4-oxo-2-substituted thiazolidin-3ylamino)ethyl)benzamide derivatives as anticonvulsant agents
Nikalje, Anna Pratima G.,Shaikh, Arfat N.,Shaikh, Sameer I.,Kalam Khan, Firoz A.,Sangshetti, Jaiprakash N.,Shinde, Devanand B.
, p. 5558 - 5562 (2015/01/08)
Herewith, we report the design and synthesis of a series of N-(2-oxo-2((4-oxo-2-substituted thiazolidin-3yl)amino)ethyl) benzamide derivatives 7(a-j) under microwave irradiation, based on four component pharmacophoric model to get structural prerequisite indispensable for anticonvulsant activity. The synthesized derivatives were investigated in maximal electroshock seizure (MES), subcutaneous pentylenetetrazole (sc-PTZ) induced seizure and neurotoxicity screening. All the test compounds were administered at a dose of 30, 100 and 300 mg/kg body weight at the time interval of 0.5 h and 4 h. The compounds were also evaluated for behavioral activity and toxicity study. The compound 7h was found to be most active in MES model. The anticonvulsant screening data shows that 65% of the compounds were found active against MES model when compared to 35% sc-PTZ model. The computational parameter such as docking study, log P determination and ADME prediction were performed to exploit the results.
Synthesis of piperazinyl benzothiazole/benzoxazole derivatives coupled with 1,3,4-oxadiazole-2-thiol: Novel hybrid heterocycles as anticancer agents
Murty,Ramalingeswara Rao,Katiki, Mohana Rao,Nath, Lekshmi R.,Anto, Ruby John
, p. 4980 - 4991 (2013/09/23)
The synthesis of a series of substituted 2-(piperazin-1-yl)benzothiazole/ benzoxazole coupled with 1,3,4-oxadiazole-2-thiol pharmacophore (8a-t) is described using a three carbon spacer (Jones and Helm, Drugs 69:1903-1910, 2009). The structures of the compounds were confirmed by NMR and mass spectral data. All the synthesized compounds have been evaluated for their cytotoxicity towards five human cancer cell lines of different origins, viz. MCF-7 (Breast), HeLa (Cervical), HepG2 (Liver), A431 (Skin) and A549 (Lung), and IC50 values were determined. Among the compounds tested, 8j and 8t displayed maximum cytotoxic activity. A431 was the most sensitive cell line against the compounds studied, followed by MCF7, A549, HepG2 and HeLa.
Synthesis and comparison of antioxidant properties of indole-based melatonin analogue indole amino acid derivatives
Suzen, Sibel,Cihaner, Seyhan Sezen,Coban, Tulay
experimental part, p. 76 - 83 (2012/05/04)
Increased levels of reactive oxygen species attributed to oxidative stress have been found to be responsible for the development of some vital diseases such as cardiovascular, neurodegenerative and autoimmune diseases. Recently, it was observed that melatonin is a highly important antioxidant, and melatonin analogues are under investigation to find out improved antioxidant activity. In this study, 14 melatonin -based analogue indole amino acid and N-protected amino acid derivatives were synthesized and elucidated spectrometrically. To investigate the antioxidant activity of the synthesized compounds and to compare with melatonin, butylhydroxytoluene and vitamin E, lipid peroxidation inhibition and 2,2-diphenyl-1-picrylhydrazyl radical-scavenging activities were tested. The results indicated that the synthesized new indole amino acid derivatives have similar activities to melatonin in 2,2-diphenyl-1-picrylhydrazyl radical-scavenging activity assay but more potent activities in lipid peroxidation inhibition assay. A series of indole-based melatonin analogue indole-amino acid and N-protected amino acid derivatives were synthesized to investigate antioxidant activity by different assays. The results indicated that the synthesized compounds have similar activities to melatonin in DPPH radical scavenging activity assay but more potent activities in lipid peroxidation inhibition assay.
