Synthesis, antifungal activity and structure-activity relationships of 2-(alkyl or aryl)-2-(alkyl or polyazol-1-ylmethyl)-4-(polyazol-1-ylmethyl)-1, 3-dioxolanes

Baji, H; Kimny, Tan; Gasquez, F.; Flammang, M.; Compagnon, Paul-Louis; Delcourt, A.; Mathieu, G.; Viossat, Β.; Morgant, Georges; Dung, Nguyen‐Huy

doi:10.1016/s0223-5234(97)83290-4

Cited by 10 publications

(9 citation statements)

References 16 publications

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“…The preparation of des -triazole ITZ analogues containing a modified triazolone region starts with direct coupling of the desired dioxolane ( 3 or 4 ) with the unprotected linker region ( 5 ) to provide key intermediate 6 or 7 . − The dioxolane-containing nitro was reduced to the aniline in the presence of 10% Pd/C and hydrazine monohydrate (Scheme ). , These key aniline intermediates ( 8 and 9 ) can be utilized to provide the most efficient synthetic route toward a diverse set of ITZ analogues that contain modifications to the triazolone/side chain region.…”

Section: Resultsmentioning

confidence: 99%

“…Des -triazole ITZ analogues containing carbamate, hydrazine carboxamide, or an unsubstituted triazolone were synthesized in a similar manner, as previously described for the synthesis of ITZ and other analogues (Scheme ). , The carbamates 37 and 38 were generated through the addition of phenyl chloroformate to anilines 8 and 9 , respectively. The addition of hydrazine monohydrate to the carbamates provided the hydrazine carboxamides 39 and 40 .…”

Section: Resultsmentioning

confidence: 99%

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Structure–Activity Relationships for Itraconazole-Based Triazolone Analogues as Hedgehog Pathway Inhibitors

et al. 2019

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The Food and Drug Administration-approved antifungal agent, itraconazole (ITZ), has been increasingly studied for its novel biological properties. In particular, ITZ inhibits the hedgehog (Hh) signaling pathway and has the potential to serve as an anticancer chemotherapeutic against several Hh-dependent malignancies. We have extended our studies on ITZ analogues as Hh pathway inhibitors through the design, synthesis, and evaluation of novel des-triazole ITZ analogues that incorporate modifications to the triazolone/side chain region of the scaffold. Our overall results suggest that the triazolone/side chain region can be replaced with various functionalities (hydrazine carboxamides and meta-substituted amides) resulting in improved potency when compared to ITZ. Our studies also indicate that the stereochemical orientation of the dioxolane ring is important for both potent Hh pathway inhibition and compound stability. Finally, our studies suggest that the ITZ scaffold can be successfully modified in terms of functionality and stereochemistry to further improve its anti-Hh potency and physicochemical properties.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Structure–Activity Relationships for Itraconazole-Based Triazolone Analogues as Hedgehog Pathway Inhibitors

et al. 2019

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“…Similarly, flow cytometry indicated that the 3,4-hexanedione derivative caused interruption in the neuroblastoma cell cycle and induced apoptosis up to 60.4±0.5% [37]. 2-benzyl-1,3-dioxolane exhibits a broad spectrum of biological activities such as antifungal [38], antibacterial [39,40], and antineoplastic [41] activities.…”

Section: Discussionmentioning

confidence: 98%

Screening of Bioprotective Properties of Various Plant Extracts and Gas Chromatography-Mass Spectrometry Profiling of Adenanthera Pavonina Stem Extract

Bhadran

George

Sudhakar

et al. 2017

Asian J Pharm Clin Res

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Objective: The search for various phytotherapeutic compounds is on rise due to a complex multifactorial phenomenon called drug resistance. The present study investigates the cytotoxic, antioxidant, and antiproliferative potential of methanolic extracts of Clitorea ternatea, Averrhoa bilimbi, Phyllanthus acidus, Tecoma stans, Curcuma aromatica, Anethum graveolens, Adhatoda vasica, Markhamia lutea, Spathodea companulata, and Adenanthera pavonina.Methods: The plant parts were extracted with methanol and screened for 1,1-diphenyl-2-picrylhydrazyl (DPPH) and 2,2’-azino-bis(3- ethylbenzothiazoline-6-sulfonic acid) (ABTS) free radical scavenging abilities. The cytotoxic activity of the extracts was investigated on HeLa and HCT116 cells through 3-(4,5-dimethylthiazol2yl)-2,5-diphenyl tetrazolium bromide (MTT) assay, and cell cycle was analyzed by flow cytometry to determine the antiproliferative activity of the extracts. The stem extract of A. pavonina was further subjected to gas chromatography-mass spectrometry (GC-MS) analysis for purification of the compounds of interest. A two-way ANOVA was done to estimate the effect of the extract between samples remembered at p<0.05 level.Results: Among all the studied samples, the extract of A. pavonina (stem) showed significant scavenging activity of 70.23% and 76.32% of scavenging compared to 74.58 % and 81.13% of that of reference standard in ABTS and DPPH assay, respectively. GC-MS analysis of the extract revealed the presence of 17 phytocompounds. MTT assay revealed that this extract (SB19) had promising cytotoxic activity against the two cancer cell lines, HCT116 and HeLa with inhibitory concentration 50% IC50 values of 25.86±0.21 μg/ml and 39.89±0.11 μg/ml, respectively. The extract treatment caused significant arrest in G2M phase of cell cycle.Conclusion: A. pavonina (stem) extract displayed significant antioxidant and antiproliferative activity and can be considered as a potential candidate drug for anticancer studies.

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“…Aryl, alkyl, imidazole, triazole, pyrazole, benzimidazole, benzotriazole, oxypurine, pyrimidinyl and naphtyl groups are linked to 1,3-dioxolane ring at different positions like 2, 4 or 5. Depending on the position of the substituents, these compounds exhibit a broad spectrum of biological activities such as antifungal [4], antibacterial [5,6], antineoplastic [7], antiviral [8,9], anesthetic [10,11] and anticonvulstant ones [12]. According to the literature survey, several 1,3-dioxolanes are used co-monomer for manufacture of polyacetals and other polymers, solvent for chemical reactions (including inorganic salts), stabilizer for halogenated organic solvents and as a starting material or reagent for organic synthesis [13].…”

Section: Introductionmentioning

confidence: 99%

Spectroscopic Aspects, Structural Elucidation, Vibrational and Electronic Investigations of 2-Methoxy-1,3-Dioxolane: An Interpretation Based on DFT and QTAIM Approach

Prabaharan¹,

Xavier²

2015

J Theor Comput Sci

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Synthesis, antifungal activity and structure-activity relationships of 2-(alkyl or aryl)-2-(alkyl or polyazol-1-ylmethyl)-4-(polyazol-1-ylmethyl)-1, 3-dioxolanes

Cited by 10 publications

References 16 publications

Structure–Activity Relationships for Itraconazole-Based Triazolone Analogues as Hedgehog Pathway Inhibitors

Structure–Activity Relationships for Itraconazole-Based Triazolone Analogues as Hedgehog Pathway Inhibitors

Screening of Bioprotective Properties of Various Plant Extracts and Gas Chromatography-Mass Spectrometry Profiling of Adenanthera Pavonina Stem Extract

Spectroscopic Aspects, Structural Elucidation, Vibrational and Electronic Investigations of 2-Methoxy-1,3-Dioxolane: An Interpretation Based on DFT and QTAIM Approach

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