888071-72-5Relevant articles and documents
Direct Access for the Regio- And Stereoselective Synthesis of N-Alkenylpyrazoles and Chromenopyrazoles
Kurma, Siva Hariprasad,Sridhar, Balasubramanian,Bhimapaka, China Raju
supporting information, p. 2271 - 2282 (2021/02/06)
A highly regio- and stereoselective method was developed for the preparation of N-alkenylpyrazoles and chromenopyrazoles by the reaction of N-tosylhydrazones and salicyl N-tosylhydrazones with alkynes under neat conditions in the presence of La(OTf)3. The present study was found to be efficient and convenient for direct access to N-alkenylpyrazoles and chromenopyrazoles through C-C, C-N, and C-O bond forming reactions. Structure assignment of N-alkenylpyrazole compound 5c was confirmed by X-ray analysis.
Biological evaluation of p-toluene sulphonylhydrazone as carbonic anhydrase IX inhibitors: An approach to fight hypoxia-induced tumors
Queen, Aarfa,Khan, Parvez,Idrees, Danish,Azam, Amir,Hassan, Md. Imtaiyaz
, p. 840 - 850 (2017/10/06)
To find potential inhibitors of human carbonic anhydrase IX (CAIX), we have successfully deigned, synthesized and characterized three p-toluene sulphonylhydrazone derivatives (1–3). Molecular docking studies provided the structural basis of CAIX inhibition and a deeper insight into the protein-ligand interactions. p-Toluene sulphonylhydrazone derivatives show a well organized conformational compatibility with the active site of CAIX. The protein-ligand complex was stabilized by several non-covalent interactions offered by residues present in the active site cavity. The actual binding affinity of synthesized compounds with CAIX was experimentally measured by fluorescence and isothermal titration calorimetry (ITC). Results of both fluorescence binding and ITC measurements show the binding affinity of p-Toluene sulphonylhydrazone derivatives to the CAIX in the μM range. CAIX enzyme inhibition assay showed the IC50 values in nM range. Though all the three compounds (1–3) showed a good binding with CAIX, compound 2 showed the best inhibition of CAIX activity. These compounds were non-toxic on normal cell lines (HEK-293) and significantly inhibit the proliferation of hypoxic cancer cells. All compounds induce apoptosis in the hypoxic cancer cells. These compounds may be further exploited as promising therapeutic agents to control the hypoxia-induced tumors.
Generation of phosphoranes derived from phosphites. A new class of phosphorus ylides leading to high E selectivity with semi-stabilizing groups in Wittig Olefinations
Aggarwal, Varinder K.,Fulton, J. Robin,Sheldon, Chris G.,De Vicente, Javier
, p. 6034 - 6035 (2007/10/03)
Tosylhydrazones derived from aryl aldehydes react with t-BuOK, ClFeTPP, (MeO)3P, and aldehydes to furnish olefins with high E selectivity. These reactions occur through a Wittig-type pathway via the corresponding diazo compounds, metal carbenes and phosphorous ylides, with the water-soluble trimethyl phosphate as the byproduct. Similar reactions can also be performed using ethyl diazoacetate; however, high E selectivity was only observed in the presence of LiBr. In this case, the reaction is believed to occur via the phosphonate anion, formed through an Arbuzov reaction. Thus this olefination reaction occurs through a Horner-Wadsworth-Emmons (HWE) reaction but the phosphonate anion is generated under completely base-free conditions. Copyright