102994-17-2Relevant academic research and scientific papers
Imidazole transfer from 1,1'-carbonyldimidazole and 1,1'- (thiocarbonyl)diimidazole to alcohols. A new protocol for the conversion of alcohols to alkylheterocycles
Totleben,Freeman,Szmuszkovicz
, p. 7319 - 7323 (1997)
The transfer of imidazole from 1,1'-carbonyldimidazole (CDI) and 1,1'- (thiocarbonyl)diimidazole in modest to excellent yields under mild conditions was observed with activated alcohols, unactivated alcohols generally providing the expected carbonylimidazole esters. Reasonable mechanisms for the transfer are proposed. 1,1'-Carbonyldi-1,2,4-triazole was found to work as well, providing a new heterocycle in good yield. Chemists should be aware of this reaction when treating benzylic, vinylogous benzylic, and benzhydryl alcohols with CDI-type reagents, expecting elimination of heterocycle rather than incorporation of heterocycle and elimination of CO2.
Sequential Selective C?H and C(sp3)?+P Bond Functionalizations: An Entry to Bioactive Arylated Scaffolds
Babu, K. Naresh,Masarwa, Ahmad,Massarwe, Fedaa,Shioukhi, Israa
, p. 26199 - 26209 (2021/11/09)
Organophosphonium salts containing C(sp3)?+P bonds are among the most utilized reagents in organic synthesis for constructing C?C double bonds. However, their use as C-selective electrophilic groups is rare. Here, we explore an efficient and general transition-metal-free method for sequential chemo- and regioselective C?H and C(sp3)?+P bond functionalizations. In the present study, C?H alkylation resulting in the synthesis of benzhydryl triarylphosphonium salts was achieved by one-pot, four-component cross-coupling reactions of simple and commercially available starting materials. The utility of the resulting phosphonium salt building blocks was demonstrated by the chemoselective post-functionalization of benzylic C(sp3)?+PPh3 groups to achieve aminations, thiolations, and arylations. In this way, benzhydrylamines, benzhydrylthioethers, and triarylmethanes, structural motifs that are present in many pharmaceuticals and agrochemicals, are readily accessed. These include the synthesis of two anticancer agents from simple materials in only two to three steps. Additionally, a protocol for late-stage functionalization of bioactive drugs has been developed using benzhydrylphosphonium salts. This new approach should provide novel transformations for application in both academic and pharmaceutical research.
Design, synthesis and antifungal activity of some new imidazole and triazole derivatives
Rezaei, Zahra,Khabnadideh, Soghra,Zomorodian, Kamiar,Pakshir, Kyvan,Kashi, Giti,Sanagoei, Narges,Gholami, Sanaz
experimental part, p. 658 - 665 (2012/06/29)
Triazole and imidazole are incorporated into the structures of many antifungal compounds. In this study a novel series of 1,2,4-triazole, imidazole, benzoimidazole, and benzotriazole derivatives was designed as inhibitors of cytochrome P450 14α-demethylase (14DM). These structures were docked into the active site of MT-CYP51, using Autodock program. Sixteen compounds with the best binding energy were synthesized. The chemical structures of the new compounds were confirmed by elemental and spectral (1H-NMR and Mass) analyses. All compounds were investigated for antifungal activity against Candida albicans, Candida tropicalis, Candida glabrata, Candida parapeilosis, Candida kruzei, Candida dubliniensis, Aspergillus fomigatus, Aspergillus flavus, Microsporum canis, Microsporum gypseum, Trichophyton mentagrophyte, Epidermophyton floccosum. Some compounds showed excellent in-vitro antifungal activity against most of the tested fungi. Compounds 2, 9, and 10 had antifungal activity against several resistant fungi against fluconazole and itraconazole. A novel series of azole derivatives was designed and synthesized as inhibitors of cytochrome P450 14α-demethylase and the compounds were investigated for antifungal activity. Copyright
Estrogen Synthetase Inhibitors. 2. Comparison of the in Vitro Aromatase Inhibitory Activity for a Variety of Nitrogen Heterocycles Substituted with Diarylmethane or Diarylmethanol Groups
Jones, C. David,Winter, Mark A.,Hirsch, Kenneth S.,Stamm, Nancy,Taylor, Harold M.,et al.
, p. 416 - 429 (2007/10/02)
The preparation and in vitro aromatase inhibitory activity of a wide variety of heterocyclic (4,4'-dichlorodiphenyl)methanes and -methanols are described.The choice of the two diaryl-bearing moieties as a vehicle for the evaluation of the heterocycles was made by the comparison of series of imidazole and pyridine-derived compunds with similar pyrimidine compounds reported previously.A structural model for the most active compounds is also presented.The activity of a related series of compounds which contain two heterocyclic moieties was found to be consistent with the model.Many of the compounds evaluated, including representatives of the pyridine, imidazole, pyrimidine, pyrazole, triazole, thiazole, and isothiazole classes, exhibit EC50 potencies for aromatase inhibition at low nanomolar levels.These compunds are at least as potent as other nonsteroidal aromatase inhibitors reported previously.
