38488-17-4Relevant academic research and scientific papers
Oxidative Sulfonylation of Hydrazones Enabled by Synergistic Copper/Silver Catalysis
Xu, Jun,Shen, Chao,Qin, Xian,Wu, Jie,Zhang, Pengfei,Liu, Xiaogang
, p. 3706 - 3720 (2021/02/05)
A copper/silver-cocatalyzed protocol for oxidative sulfonylation of hydrazones is demonstrated. A wide range of β-ketosulfones and N-acylsulfonamides are directly synthesized in moderate to good yields. Our work provides a viable method for scalable preparation of β-ketosulfone derivatives that have found wide applications in the pharmaceutical industry.
One-pot synthesis of chiral β-hydroxysulfones from alkynes: Via aerobic oxysulfonylation and asymmetric reduction in MeOH/H2O
Cui, Peng,Liu, Qixing,Wang, Juan,Liu, Huan,Zhou, Haifeng
supporting information, p. 634 - 639 (2019/02/14)
A highly enantioselective synthesis of β-hydroxysulfones from inexpensive and readily available terminal alkynes and sodium sulfinates via a consecutive one-pot reaction in an aqueous medium under mild conditions is described. The intermediates, β-keto sulfones, generated from an aerobic oxysulfonylation of terminal alkynes and sodium sulfinates catalyzed by an iron salt in MeOH/H2O (v : v = 3 : 1) at 50 °C, were subsequently reduced by a Ru-catalyzed asymmetric transfer hydrogenation with HCOONa as a hydrogen source. A variety of chiral β-hydroxysulfones were obtained in good yields and up to 99.9% ee values. This one-pot process could be easily scaled up for gram-scale synthesis.
Dual-tail arylsulfone-based benzenesulfonamides differently match the hydrophobic and hydrophilic halves of human carbonic anhydrases active sites: Selective inhibitors for the tumor-associated hCA IX isoform
Ibrahim, Hany S.,Allam, Heba Abdelrasheed,Mahmoud, Walaa R.,Bonardi, Alessandro,Nocentini, Alessio,Gratteri, Paola,Ibrahim, Eslam S.,Abdel-Aziz, Hatem A.,Supuran, Claudiu T.
, p. 1 - 9 (2018/04/25)
The synthesis and characterization of two new sets of arylsulfonehydrazone benzenesulfonamides (4a-4i with phenyl tail and 4j-4q with tolyl tail) are reported. The compounds were designed according to a dual-tails approach to modulate the interactions of the ligands portions at the outer rim of both hydrophobic and hydrophilic active site halves of human isoforms of carbonic anhydrase (CA, EC 4.2.1.1). The synthesized sulfonamides were evaluated in vitro for their inhibitory activity against the following human (h) isoforms, hCA I, II, IV and IX. With the latter being a validated anticancer drug target and a marker of tumor hypoxia, attractive results arose from the Compounds’ inhibitory screening in terms of potency and selectivity. Indeed, whereas the first subset of compounds 4a-4i exhibited great efficacy in inhibiting both the ubiquitous, off-target hCA II (KIs 9.5–172.0 nM) and hCA IX (KIs 7.5–131.5 nM), the second subset of tolyl-bearing derivatives 4j-4q were shown to possess a selective hCA IX inhibitory action over isoforms I, II and IV. The most selective compounds 4l and 4n were further screened for their in vitro cytotoxic activity against MCF-7 and MDA-MB-231 cancer cell lines under hypoxic conditions. The selective IX/II inhibitory trend of 4j-4q compared to those of compounds 4a-4i was unveiled by docking studies. Further exploration of these molecules could be useful for the development of novel antitumor agents with a selective CA inhibitory mechanism.
Visible-light initiated direct oxysulfonylation of alkenes with sulfinic acids leading to β-ketosulfones
Yang, Daoshan,Huang, Ben,Wei, Wei,Li, Jin,Lin, Gu,Liu, Yaru,Ding, Jiehua,Sun, Pengfei,Wang, Hua
supporting information, p. 5630 - 5634 (2016/10/22)
Visible light along with 1 mol% eosin Y catalyzed the direct oxysulfonylation of alkenes with sulfinic acids via a photoredox process which has been developed at room temperature under transition-metal-free conditions. The present reaction provides a highly efficient approach to diverse β-ketosulfones in moderate to good yields. It should provide a promising synthesis candidate for the formation of diverse and useful β-ketosulfone derivatives in the fields of synthetic and pharmaceutical chemistry.
Iron-Catalyzed Oxidative Sulfonylation of Enol Acetates: An Environmentally Benign Approach to β-Keto Sulfones
Yadav, Vinod K.,Srivastava, Vishnu P.,Yadav, Lal Dhar S.
, p. 427 - 431 (2016/02/09)
The first application of iron-catalyzed sulfonylation of aryl enol acetates with sulfonyl hydrazides for the construction of β-keto sulfones under aerobic conditions is reported. The present protocol, which utilizes an inexpensive iron salt as the catalyst, readily available sulfonyl hydrazides as the sulfonylating reagents, and air as oxidant under mild conditions, provides a cost-effective and environmentally benign approach to various β-keto sulfones.
Chemoselective one-pot synthesis of β-keto sulfones from ketones
Rawat, Vikas S.,Reddy, Perla L. M.,Sreedhar, Bojja
, p. 5165 - 5168 (2014/01/23)
A practical method to synthesize substituted β-keto sulfones directly from ketones at room temperature has been developed. This method involves the nucleophilic addition of a base generated enolate to sulfonyl iodide. The reaction shows high chemoselectivity for the addition of a sulfonyl group to an α-carbon over a hydroxyl group. In addition, the given protocol provides good to excellent yields of β-keto sulfones under mild reaction conditions. Moreover, the regiochemical aspect of the protocol is also explored.
Manganese(III) acetate-mediated oxidative cyclization of α-methylstyrene and trans-stilbene with β-ketosulfones
Bouhlel, Ahlem,Curti, Christophe,Tabele, Clemence,Vanelle, Patrice
, p. 4293 - 4307 (2013/06/04)
A convenient microwave irradiation protocol was utilized for the synthesis of β-ketosulfones 1-5 in good yields. These sulfones reacted with alkenes through a radical oxidative cyclization mediated by Mn(OAc)3. Dihydrofurans 6-10 were obtained
Multicomponent reactions of β-ketosulfones and formaldehyde in a bio-based binary mixture solvent system composed of meglumine and gluconic acid aqueous solution
Yang, Jie,Li, Haoquan,Li, Minghao,Peng, Jiajian,Gu, Yanlong
supporting information; experimental part, p. 688 - 700 (2012/04/23)
A mixture of two bio-based chemicals, meglumine and gluconic acid aqueous solution (GAAS, 50 wt%), was demonstrated to be a task-specific bio-based solvent for performing the hydroxymethylation of β-ketosulfones with formaldehyde. The formed hydroxymethylation product could further react with a nucleophile, which allowed us to develop some one-pot, stepwise, three-component reactions of β-ketosulfones and formaldehyde in this binary mixture. Particularly, a one-pot, two-step, sequential four-component reaction of α-bromo ketone, sodium benzenesulfinate, thiophenol and formaldehyde was also developed. These results not only demonstrate that it is possible to develop a new bio-based system by mixing two or more bio-based chemicals together, but also confer us a convenient means for controlling the selectivity of some multicomponent reactions of formaldehyde. Because GAAS and meglumine are both highly hydrophilic, the mixed solvent system could thus be recovered after extraction of organic products. In a three-component reaction of β-ketosulfone, paraformaldehyde and α-methylstyrene, the GAAS/meglumine system could be reused at least four times without significant loss of activity. Copyright
Microwave-assisted manganese(III) acetate based oxidative cyclizations of alkenes with β-ketosulfones
Curti, Christophe,Crozet, Maxime D.,Vanelle, Patrice
experimental part, p. 200 - 205 (2009/04/07)
The microwave-assisted synthesis of 5-(4-nitrophenyl)-2-phenyl-4-(phenylsulfonyl)-2,3-dihydrofuran (5a) was performed via manganese(III) acetate based oxidative cyclization of 1-(4-nitrophenyl)-2-(phenylsulfonyl)ethanone (3a) with vinylbenzene (4a). This
β-Keto sulfones as inhibitors of 11β-hydroxysteroid dehydrogenase type I and the mechanism of action
Xiang, Jason,Ipek, Manus,Suri, Vipin,Tam, May,Xing, Yuzhe,Huang, Nelson,Zhang, Yanling,Tobin, James,Mansour, Tarek S.,McKew, John
, p. 4396 - 4405 (2008/03/12)
The design, synthesis, and biological evaluation of β-keto sulfones as 11β-HSD1 inhibitors and the mechanism of inhibition are described here. This class of compounds is not active against 11β-HSD2 and therefore may have therapeutic potential for metabolic syndrome and type 2 diabetes.
