53560-25-1Relevant academic research and scientific papers
Synthesis, in vitro and in silico evaluation of diaryl heptanones as potential 5LOX enzyme inhibitors
Meka, Bharani,Ravada, Suryachandra Rao,Muthyala, Murali Krishna Kumar,Kurre, Purna Nagasree,Golakoti, Trimurtulu
, p. 408 - 421 (2018/07/13)
A new series of diaryl heptanones (12a-q) were synthesized and their structures were confirmed by its 1H, 13C NMR and Mass spectral data. These analogs were evaluated for their anti-oxidant activity and potential to inhibit 5-lipoxygenase. Compounds 12k and 12o showed potent in vitro 5-lipoxygenase enzyme inhibitory activity with IC50 values of 22.2, 21.5 μM, which are comparable to curcumin (24.4 μM). Further they also have shown significant antioxidant activity. Molecular docking studies clearly showed correlation between binding energy and potency of these compounds.
Synthesis, urease and acetylcholine esterase inhibition activities of some 1,4-disubstituted thiosemicarbazides and their 2,5-disubstituted thiadiazoles
Saleem, Muhammad,Rafiq, Muhammad,Hanif, Muhammad,Rama, Nasim Hasan,Seo, Sung-Yum,Lee, Ki-Hwan
, p. 2741 - 2747 (2012/10/29)
A new series of 2,5-disubstituted-1,3,4-thiadiazoles 6a-i was synthesized by overnight stirring various 1,4-disubstituted thiosemicarbazides 5a-i in polyphosphoric acid followed by neutralization. The structures of newly synthesized compounds 5a-i and 6a-i were characterized by IR, 1H and 13C NMR, elemental analysis and mass spectrometric studies. All the synthesized compounds were evaluated for their urease and acetylcholine esterase inhibition activities. Thiosemicarbazides 5a-i are found to possess excellent potential for urease inhibition, more than the standard drug. Thiosemicarbazides 5a-i are more potent urease inhibitor than their cyclic analogues thiadiazoles 6a-i. Almost all of the compounds are excellent inhibitors of acetylcholine esterase. The inhibition of acetylcholine esterase of compounds 5a, 5c, 5d, 5g, 5i, 6e, 6f, 6g, and 6i is much more than that of standard drug.
Synthesis, acetylcholinesterase and alkaline phosphatase inhibition of some new 1,2,4-triazole and 1,3,4-thiadiazole derivatives
Khan, Imtiaz,Hanif, Muhammad,Rama, Nasim Hasan,Hussain, Muhammad Tahir,Khan, Aftab Ahmed,Aslam, Muhammad Adil S.,Iqbal, Jamshed
, p. 1413 - 1419,7 (2020/09/02)
A new series of 4,5-disubstituted-2,4-dihydro-3H-1,2,4-triazole-3-thiones (6as) and 2,5-disubstituted-1,3,4-thiadiazoles (7ah) was synthesized by intramolecular dehydrocyclization of various 1,4-disubstituted thiosemicarbazide derivatives (5as) by refluxing in 4N aqueous sodium hydroxide and by overnight stirring with polyphosphoric acid, respectively. The structures of these compounds were characterized by IR, 1H and 13C NMR, elemental analysis and mass spectroscopic studies. All the synthesized compounds were screened for their acetylcholinesterase and alkaline phosphatase inhibition studies. Most of the tested compounds showed promising activities, amongst them (6k) and (6q) showed excellent acetylcholinesterase inhibitory activity with IC50 0.2410.012 and 0.2600.013M, respectively, as compared with those of standard drug whereas the compound (6p), with IC50 0.0440.001M, was found to be the most potent inhibitor of alkaline phosphatase.
Structure-activity relationships of phenylpropanoids as antifeedants for the pine weevil Hylobius abietis
Bohman,Nordlander,Nordenhem,Sunnerheim,Borg-Karlson,Unelius
, p. 339 - 352 (2008/09/18)
Ethyl cinnamate has been isolated from the bark of Pinus contorta in the search for antifeedants for the pine weevil, Hylobius abietis. Based on this lead compound, a number of structurally related compounds were synthesized and tested. The usability of the Topliss scheme, a flow diagram previously used in numerous structure-activity relationship (SAR) studies, was evaluated in an attempt to find the most potent antifeedants. The scheme was initially followed stepwise; subsequently, all compounds found in the scheme were compared. In total, 51 phenylpropanoids were tested and analyzed for SARs by using arguments from the field of medicinal chemistry (rational drug design). Individual Hansch parameters based on hydrophobicity, steric, and electronic properties were examined. The effects of position and numbers of substituents on the aromatic ring, the effects of conjugation in the molecules, and the effects of the properties of the parent alcohol part of the esters were also evaluated. It proved difficult to find strong SARs derived from single physicochemical descriptors, but our study led to numerous new, potent, phenylpropanoid antifeedants for the pine weevil. Among the most potent were methyl 3-phenylpropanoates monosubstituted with chloro, fluoro, or methyl groups and the 3,4-dichlorinated methyl 3-phenylpropanoate.
Synthesis of new allocolchicinoids with seven- and eight-membered B-rings by enyne ring-closing metathesis
Boyer, Francois-Didier,Hanna, Issam
experimental part, p. 4938 - 4948 (2009/06/06)
Total syntheses of allocolchicines 4 and 5, with the ester functionality in the C-ring at the C10 or C11 positions, is reported. An asymmetric synthesis of (7S)-allocolchicine 5 is also described. The main features included the elaboration of a common int
Synthesis of allocolchicines using sequential ring-closing enyne metathesis - Diels - Alder reactions
Boyer, Francois-Didier,Hanna, Issam
, p. 715 - 718 (2007/10/03)
New allocolchinoids having functionality in the C ring at position C10 or C11 have been synthesized using the enyne ring-closing metathesis (RCM) reaction for construction of the seven-membered ring and a Diels-Alder-aromatization sequence for the elabora
Synthesis of the tricyclic core of colchicine via a dienyne tandem ring-closing metathesis reaction
Boyer, Francois-Didier,Hanna, Issam
, p. 2293 - 2295 (2008/02/05)
The synthesis of the tricyclic framework of colchicine has been achieved using a tandem ring-closing metathesis reaction of dienynes as the key step. In this process, both seven-membered rings B and C were formed in one step. Oxidation of tertiary allylic
Quantitative structure-activity relationships of pine weevil antifeedants, a multivariate approach
Sunnerheim, Kerstin,Nordqvist, Anneli,Nordlander, Goeran,Borg-Karlson, Anna-Karin,Unelius, C. Rickard,Bohman, Bjoern,Nordenhem, Henrik,Hellqvist, Claes,Karlen, Anders
, p. 9365 - 9372 (2008/03/17)
Antifeedant activity of mainly phenylpropanoic, cinnamic, and benzoic acids esters was tested on the pine weevil, Hylobius abietis (L.). Of 105 compounds screened for activity, 9 phenylpropanoates, 3 cinnamates, and 4 benzoates were found to be highly active antifeedants. To understand the structure-activity relationships of these compounds, a multivariate analysis study was performed. A number of molecular and substituent descriptors were calculated and correlated to results from two-choice feeding tests with H. abietis. Three local models were developed that had good internal predictive ability. External test sets showed moderate predictivity. In general, low polarity, small size, and high lipophilicity were characteristics for compounds having good antifeedant activity.
Novel heterobivalent tacrine derivatives as cholinesterase inhibitors with notable selectivity toward butyrylcholinesterase
Elsinghorst, Paul W.,González Tanarro, Camino M.,Gütschow, Michael
, p. 7540 - 7544 (2007/10/03)
Two series of novel heterobivalent tacrine derivatives were synthesized. A trimethoxy substituted benzene was linked to the tacrine moiety by a hydrazide-based linker. The compounds were evaluated as cholinesterase inhibitors, and trimethoxybenzoic acid derivatives with 11- or 12-atom spacers were the most potent inhibitors of human acetylcholinesterase. The inhibitors showed a surprising selectivity toward human butyrylcholinesterase, where several trimethoxyphenylpropionic acid derivatives had IC50 values less than 250 pM.
Solid-supported green synthesis of substituted hydrocinnamic esters by focused microwave irradiation
Kumar, Vinod,Sharma, Anuj,Sinha, Arun K.
, p. 483 - 495 (2007/10/03)
An efficient chemoselective hydrogenation protocol for substituted cinnamic esters is developed for the synthesis in quantitative yield of corresponding bioactive dihydrocinnamic esters with solid-supported palladium chloride/ammonium formate (cat.) in HCOOH/H2O 1:2 as a hydrogenating agent under focused-microwave irradiation for 10 min.
