305-12-4Relevant articles and documents
Synthesis of Novel Antiviral Ferulic Acid-Eugenol and Isoeugenol Hybrids Using Various Link Reactions
Gan, Xiuhai,Wang, Zhengxing,Hu, Deyu
, p. 13724 - 13733 (2021/11/23)
To develop novel antiviral agents, some novel conjugates between ferulic acid and eugenol or isoeugenol were designed and synthesized by the link reaction. The antiviral activities of compounds were evaluated using the half leaf dead spot method. Bioassay results showed acceptable antiviral activities of some conjugates against the tobacco mosaic virus (TMV) and cucumber mosaic virus (CMV). Compounds A9, A10, E1, and E4 showed remarkable curative, protective, and inactivating effects on TMV and CMV at 500 μg mL-1. Notably, these compounds exhibited excellent protective effects on TMV and CMV. The EC50 values of compounds A9, A10, E1, and E4 against TMV were 180.5, 169.5, 211.4, and 135.5 μg mL-1, respectively, and those against CMV were 210.5, 239.1, 218.4, and 178.6 μg mL-1, respectively, which were superior to those of ferulic acid (471.5 and 489.2 μg mL-1), eugenol (456.3 and 463.2 μg mL-1), isoeugenol (478.4 and 487.5 μg mL-1), and ningnanmycin (246.5 and 286.6 μg mL-1). Then, the antiviral mechanisms of compound E4 were investigated by determining defensive enzyme activities and multi-omics analysis. The results indicated that compound E4 resisted the virus infection by enhancing defensive responses via inducing the accumulation of secondary metabolites from the phenylpropanoid biosynthesis pathway in tobacco.
Novel N-4-Piperazinyl Ciprofloxacin-Ester Hybrids: Synthesis, Biological Evaluation, and Molecular Docking Studies
Mahdavi, M.,Mostafavi, H.,Shahbazi, A.,Zarrini, G.
, p. 1558 - 1565 (2020/09/21)
Abstract: A series of novel N-4-piperazinylciprofloxacin-ester hybrids has been synthesized and the structures confirmed by1H and 13C NMR, FT-IRspectral data, and elemental analysis. The products have been tested in vitro for their antibacterial activity againstsix bacterial strains (MRSA, Staphylococcusepidermidis, Bacillussubtilis, Escherichia coli,Salmonella enterica, and Klebsiella pneumoniae) and have demonstrated goodantibacterial activity with MIC values range 6.25–200 μg/mL. Antifungal andcytotoxic activities of the products have been tested against Candida kefyr and human leukemia K562 cell line,respectively. All compounds inhibit growth of K562 cells more efficiently thanthe parent ciprofoxacin in a dose- and duration-dependent way. Molecular dockingstudies performed for the compound 3i indicatesthat similarly to ciprofloxacin it can act as an inhibitor of S. aureus DNA gyrase.
Novel ketoprofen–antioxidants mutual codrugs as safer nonsteroidal anti-inflammatory drugs: Synthesis, kinetic and pharmacological evaluation
Sehajpal, Shikha,Prasad, Deo Nandan,Singh, Rajesh K.
, (2019/07/03)
Ketoprofen belongs to one of the most common nonsteroidal anti-inflammatory drugs (NSAIDs) but its clinical usefulness has been restricted due to the high incidence of gastrointestinal complications. The release of reactive oxygen species (ROS) in NSAIDs
Substituted phenyl[(5-benzyl-1,3,4-oxadiazol-2-yl)sulfanyl]acetates/acetamides as alkaline phosphatase inhibitors: Synthesis, computational studies, enzyme inhibitory kinetics and DNA binding studies
Iqbal,Ashraf,Hassan, Mubashir,Abbas,Jabeen, Erum
, (2019/07/09)
Substituted phenyl[(5-benzyl-1,3,4-oxadiazol-2-yl)sulfanyl]acetates/acetamides 9a-j were synthesized as alkaline phosphatase inhibitors. Phenyl acetic acid 1 through a series of reactions was converted into 5-benzyl-1,3,4-oxadiazole-2-thione 4. The intermediate oxadiazole 4 was then reacted with chloroacetyl derivatives of phenols 6a-f and anilines derivatives 8a-d to afford the title oxadiazole derivatives 9a-j. All of the title compounds 9a-j were evaluated for their inhibitory activity against human alkaline phosphatise (ALP). It was found that compounds 9a-j exhibited good to excellent alkaline phosphatase inhibitory activity especially 9h displayed potent activity with IC50 value 0.420 ± 0.012 μM while IC50 value of standard (KH2PO4) was 2.80 μM. The enzyme inhibitory kinetics of most potent inhibitor 9h was determined by Line-weaever Burk plots showing non-competitive mode of binding with enzyme. Molecular docking studies were performed against alkaline phosphatase enzyme (1EW2) to check the binding affinity of the synthesized compounds 9a-j against target protein. The compound 9h exhibited excellent binding affinity having binding energy value (?7.90 kcal/mol) compared to other derivatives. The brine shrimp viability assay results proved that derivative 9h was non-toxic at concentration used for enzyme assay. The lead compound 9h showed LD50 106.71 μM while the standard potassium dichromate showed LD50 0.891 μM. The DNA binding interactions of the synthesized compound 9h was also determined experimentally by spectrophotometric and electrochemical methods. The compound 9h was found to bind with grooves of DNA as depicted by both UV–Vis spectroscopy and cyclic voltammetry with binding constant values 7.83 × 103 and 7.95 × 103 M?1 respectively revealing significant strength of 9h-DNA complex. As dry lab and wet lab results concise each other it was concluded that synthesized compounds, especially compound 9h may serve as lead compound to design most potent inhibitors of human ALP.
Synthesis and evaluation of antioxidant-S-(+)-ibuprofen hybrids as gastro sparing NSAIDs
Chandiran, Senthil,Vyas, Sandeep,Sharma, Neetika,Sharma, Manu
, p. 1006 - 1016 (2014/01/06)
Ibuprofen is one of the most popular NSAIDs for the last three decades but also known for its gastrointestinal side effects similar to other NSAIDs. To overcome this problem, we have designed and synthesized ibuprofen - antioxidant (thymol, guaiacol, eugenol, and menthol) hybrids (6-13) with and without spacer as gastro sparing agents. The hybrids have been found to be chemically stable, biolabile and exhibited retention of anti-inflammatory and analgesic activity with significant reduced ulcerogenicity as compared to the ibuprofen and ibuprofen + antioxidant physical mixture. The absence of ulcerogenicity may be attributed to antioxidants and improved physicochemical properties of these hybrid molecules.
Design, synthesis and evaluation of diclofenac-antioxidant mutual prodrugs as safer NSAIDs
Manon, Benu,Sharma, Pritam D.
experimental part, p. 1279 - 1287 (2010/02/27)
Diclofenac has been conjugated with different antioxidants having antiulcerogenic activity with the objective of obtaining diclofenac-antioxidant mutual prodrugs as safer NSAIDs devoid of ulcerogenic side-effects. The synthesized derivatives are screened
Mutual prodrugs of 4-biphenylacetic acid and phytophenolics as safer NSAIDs - Synthetic and spectral studies
Sharma, Pritam Dev,Kaur, Gurbinder,Kansal, Sumeet,Chandiran, Senthil Kumar
, p. 2159 - 2164 (2007/10/03)
4-Biphenylacetic acid (4-BPA), the active metabolite of NSAID fenbufen has been modified using mutual prodrug approach. Number of 4-BPA derivatives have been synthesised as potential mutual prodrugs by the attachment of several phytophenols/alcohol as pro
