10393-86-9Relevant articles and documents
CuCl2-promoted decomposition of sulfonyl hydrazides for the synthesis of thiosulfonates
Kim, Junsu,Park, Sanggil,Kim, Hyungjun,Kim, Jinho
, (2020)
Sulfonyl hydrazides recently received much attention as reagents for the introduction of sulfur-containing functional groups into organic compounds, because both sulfonyl and sulfenyl sources could be generated by the oxidation and decomposition of the sulfonyl hydrazides, respectively. However, the transformations of sulfonyl hydrazides into thiosulfonates, which could be produced by the reaction between sulfonyl and sulfenyl sources, have been less investigated. In this manuscript, we describe CuCl2-promoted selective synthesis of thiosulfonates from sulfonyl hydrazides. A variety of thiosulfonates were produced in moderate to good yields. The mechanism involving radical intermediates such as sulfonyl radical and thiyl radical was proposed on the basis of the previously reported references and mechanistic investigations. In addition, quantum chemical simulations revealed that Cu-promoted decomposition of sulfonyl hydrazides is thermodynamically viable in the developed conditions.
An Electrochemical Variant in the Syntheses of Exaltone and Muscone: Anodic Fragmentation of α,β-Unsaturated Tosylhydrazones
Limacher, Liviana L.,Delay, Francois D.,Bedert, Nicole,Tissot, Paul
, p. 1383 - 1389 (1989)
Ring enlargement of bicyclopentadec-1(12)-en-13-one p-toluenesulfonylhydrazone into cyclopentadec-4-yn-1-one was accomplished under mild and controlled anodic oxidation conditions.The mechanism of this fragmentation is reconsidered.
Synthesis, structural properties, enzyme inhibition and molecular docking studies of (Z)-N'-(1-allyl-2-oxoindolin-3-ylidene) methanesulfono-hydrazide and (Z)-N'-(1-allyl-2-oxoindolin-3-ylidene)-3-nitrobenzenesulfono-hydrazide
Ahmed, Kainat,Arshad, Muhammad,Arshad, Muhammad Nadeem,Asiri, Abdullah M.,Iqbal, Zafar,Mahmood, Tariq,Rashid, Umer
, (2020)
Isatin and its derivatives exhibit broad range of biological and pharmacological applications. Keeping in view the importance of isatin and its derivatives, herein we report two isatin based new sulfono-hydrazides 4 & 5, synthesized in high yields and characterized by spectroscopic techniques. Their structures are confirmed unequivocally using X-ray diffraction crystallography, which revealed the presence of P21/c (4) and P21/n (5) space groups and unit cells stabilized through noncovalent interactions. Further details about geometric and electronic properties of compounds 4 and 5 are obtained by quantum mechanical approach based on density functional theory (DFT). These compounds are also evaluated for in vitro urease enzyme inhibition potential against Bacillus pasteurii. Both compounds inhibited the urease activity in μM concentration, however, compound 4 with IC50 value of 15.26 ± 0.16 μM proved to be more potent than the standard thiourea having IC50 value of 21.25 ± 0.15 μM. The higher inhibition activity of compound 4 might be associated with its stronger interaction as observed by in silico molecular docking studies using MOE, which showed that compound 4 interacts more closely to the binding site of enzyme (4UBP) via Ni2+ ions coordination as compared to its counterpart.
One-pot synthesis of sulfonylhydrazones from sulfonyl chloride, hydrazine hydrate and vinyl azide in water
Luo, Mengqiang,Wang, Hai,Ren, Xiaorong,Lu, Ruijuan,Qi, Chenze,Zhang, Yaohong,Shen, Runpu
, p. 2713 - 2722 (2021/03/19)
A facile and eco-friendly protocol for the synthesis of sulfonylhydrazones from sulfonyl chlorides, hydrazine hydrate and vinyl azides was developed. The unique advantage of this approach is that desired products can be obtained efficiently in water, which meets the requirements of green chemistry and provides good perspectives for the sustainable production of new drug candidate. Also, this reaction proceeded in moderate to good yields with a wide tolerance of functional groups.
Synthesis, in vitro α-amylase inhibitory, and radicals (DPPH & ABTS) scavenging potentials of new N-sulfonohydrazide substituted indazoles
Rafique, Rafaila,Khan, Khalid Mohammed,Arshia,Chigurupati, Sridevi,Wadood, Abdul,Rehman, Ashfaq Ur,Salar, Uzma,Venugopal, Vijayan,Shamim, Shahbaz,Taha, Muhammad,Perveen, Shahnaz
, (2019/11/26)
Over-expression of α-amylase enzyme causes hyperglycemia which lead to many physiological complications including oxidative stress, one of the most commonly associated problem with diabetes mellitus. Marketed α-amylase inhibitors such as acarbose, voglibose, and miglitol used to treat type-II diabetes mellitus, but also linked to several harmful effects. Therefore, it is essential to explore new and nontoxic antidiabetic agents with additional antioxidant properties. In this connection, a series of new N-sulfonohydrazide substituted indazoles 1–19 were synthesized by multistep reaction scheme and assessed for in vitro α-amylase inhibitory and radical (DPPH and ABTS) scavenging properties. All compounds were fully characterized by different spectroscopic techniques including 1H, 13C NMR, EI-MS, HREI-MS, ESI-MS, and HRESI-MS. Compounds showed promising α-amylase inhibitory activities (IC50 = 1.23 ± 0.06–4.5 ± 0.03 μM) as compared to the standard acarbose (IC50 1.20 ± 0.09 μM). In addition to that all derivatives were found good to moderate scavengers of DPPH (IC50 2.01 ± 0.13–5.3 ± 0.11) and ABTS (IC50 = 2.34 ± 0.07–5.5 ± 0.07 μM) radicals, in comparison with standard ascorbic acid having scavenging activities with IC50 = 1.99 ± 0.09 μM, and IC50 2.03 ± 0.11 μM for DPPH and ABTS radicals. In silico molecular docking study was conducted to rationalize the binding interaction of α-amylase enzyme with ligands. Compounds were observed as mixed type inhibitors in enzyme kinetic characterization.
