- Modular Synthesis of Carbon-Substituted Furoxans via Radical Addition Pathway. Useful Tool for Transformation of Aliphatic Carboxylic Acids Based on "build-and-Scrap" Strategy
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Utilizing radical chemistry, a new general C-C bond formation on the furoxan ring was developed. By taking advantage of the lability of furoxans, a wide variety of transformation of the synthesized furoxans have been demonstrated. Thus, this developed methodology enabled not only the modular synthesis of furoxans but also short-step transformations of carboxylic acids to a broad range of functional groups.
- Matsubara, Ryosuke,Kim, Hojin,Sakaguchi, Takaya,Xie, Weibin,Zhao, Xufeng,Nagoshi, Yuto,Wang, Chaoyu,Tateiwa, Masahiro,Ando, Akihiro,Hayashi, Masahiko,Yamanaka, Masahiro,Tsuneda, Takao
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p. 1182 - 1187
(2020/02/15)
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- Synthesis and Pharmacological Activity of Tris(2-hydroxyethyl)ammonium 4-Chlorophenylsulfonylacetate
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Methods for the synthesis of 4-chlorophenylsulfonylacetic acid and its tris(2-hydroxyethyl)ammonium salt (“sulfacetamine”) were studied. The results of in vitro and in vivo experiments showed that sulfacetamine possesses high antithrombotic, antioxidant, hypocholesterolemic, immunostimulating, and protective-adaptive activities.
- Adamovich,Oborina,Mirskova
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p. 701 - 705
(2018/07/06)
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- Synthesis and antioxidant activity of bis unsaturated sulfones, bis pyrroles, and bis pyrazoles
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The Michael acceptor 1,4-bis-(E)-2-(arylsulfonylvinyl)benzene was exploited to prepare a new series of bis heterocycles-(1,4-phenylene)bis(arylsulfonylpyrrole) and (1,4-phenylene)bis(arylsulfonyl pyrazole). All of the compounds were tested for antioxidant activity. Amongst the tested compounds, 1,4-bis-(E)-2-(arylsulfonylvinyl)benzene (5) was found to be the best potential antioxidant agent.
- Lavanya,Prakash, T. Bhanu,Sravya,Padmavathi,Padmaja
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p. 8815 - 8828
(2015/10/28)
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- Discovery of 8-cyclopentyl-2-[4-(4-methyl-piperazin-1-yl)-phenylamino]-7- oxo-7,8-dihydro-pyrido[2,3- d ]pyrimidine-6-carbonitrile (7x) as a potent inhibitor of cyclin-dependent kinase 4 (CDK4) and AMPK-related kinase 5 (ARK5)
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The success of imatinib, a BCR-ABL inhibitor for the treatment of chronic myelogenous leukemia, has created a great impetus for the development of additional kinase inhibitors as therapeutic agents. However, the complexity of cancer has led to recent interest in polypharmacological approaches for developing multikinase inhibitors with low toxicity profiles. With this goal in mind, we analyzed more than 150 novel cyano pyridopyrimidine compounds and identified structure-activity relationship trends that can be exploited in the design of potent kinase inhibitors. One compound, 8-cyclopentyl-2-[4-(4-methyl- piperazin-1-yl)-phenylamino]-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidine-6- carbonitrile (7x), was found to be the most active, inducing apoptosis of tumor cells at a concentration of approximately 30-100 nM. In vitro kinase profiling revealed that 7x is a multikinase inhibitor with potent inhibitory activity against the CDK4/CYCLIN D1 and ARK5 kinases. Here, we report the synthesis, structure-activity relationship, kinase inhibitory profile, in vitro cytotoxicity, and in vivo tumor regression studies by this lead compound.
- Reddy, M. V. Ramana,Akula, Balireddy,Cosenza, Stephen C.,Athuluridivakar, Saikrishna,Mallireddigari, Muralidhar R.,Pallela, Venkat R.,Billa, Vinay K.,Subbaiah, D. R. C. Venkata,Bharathi, E. Vijaya,Vasquez-Del Carpio, Rodrigo,Padgaonkar, Amol,Baker, Stacey J.,Reddy, E. Premkumar
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p. 578 - 599
(2014/03/21)
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- Mass spectra of arylsulphonylacetic acids and correlation of fragment ions with substituent constants
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The mass spectral studies of arylsulphonylacetic acids reveal that the skeletal rearrangement via aryl-oxygen bond formation is predominant with a weak competing alkyl migration.A linear correlation is obtained between the intensities of + ions, i.e. +> and the Hammett substituent constants.
- Srinavasan, C.,Ganesan, P. K.,Shunmugasundaram, A.,Vairamani, M.
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p. 141 - 145
(2007/10/02)
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- SYNTHESIS OF ORGANOSULFONYLACETIC ACID
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Alkylsulfonylacetic acids and their esters were obtained by the alcoholysis of alkyl β,β-dichlorovinyl sulfones and the oxidation of alkylthioacetic acids.Arylsulfonylacetic acids were synthesized by the reaction of sodium arenesulfinates with monochloroacetic acid.The optimum conditions for the reaction were obtained.Arylsulfonylacetic esters were obtained by the reaction of monochloroacetic esters with sodium arenesulfinate in DMFA, and their hydrolysis led to the corresponding acids with yields of 65-98percent.Dichloroacetic estersreacts with arenesulfinates, forming di(arylsulfonyl)acetic esters.
- Mirskova, A.N.,Kryukova, Yu.I.,Levkovskaya, G.G.,Guseva, S.A.,Voronkov, M.G.
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p. 545 - 550
(2007/10/02)
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- MODERN FRIEDEL-CRAFTS CHEMISTRY. XI. CYCLIZATION OF ARYL HALOALKYL SULFONES, ARYLSULFONYLACYL CHLORIDES AND THEIR CORRESPONDING SULFIDES
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The sulfone group deactivation for cyclialkylation and cycliacylation reactions in the presence of Friedel-Crafts catalysts was demonstrated in a number of aryl chloroalkylsulfones (1-8) and arylsulfonylacyl chlorides (17a-22a), respectively.As expected, the corresponding arylchloroalkyl sulfides (9-16) and arylmercaptoacyl chlorides (13a-28a) underwent ring-closure reaction in most cases under the same conditions.The ease of cyclization was governed by the ring size, the stability of the attacking carbocation and the nucleophilicity of the aryl moiety.Also, the behaviour of benzyl sulfones (29, 31a, and 32a) and sulfides (33, 34a and 36a) was inconsistent.Noteworthy, the Friedel-Crafts cyclization reaction is thus considered an accessible method for the synthesis of compounds 37-41 and 45, 51.
- Abdel-Wahab, Aboel-Magd A.,El-Khawaga, Ahmed M.,El-Zohry, Maher F.,Khalaf, Ali A.
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