55710-19-5Relevant academic research and scientific papers
COMPOSITION, SYNTHESIS, AND USE OF NEW ARYLSULFONYL ISONITRILES
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Paragraph 0153, (2015/09/23)
This invention relates to novel isonitriles, including arylsulfonyl isonitriles, and methods for their synthesis. The isonitriles include a conjugated ring system. The structure is designed with the flexibility to have multiple substitution patterns. The isonitriles may be used in applications including, but not limited to, pharmaceutical compositions.
Alkyl sulfinates: Formal nucleophiles for synthesizing TosMIC analogs
Lujan-Montelongo, J. Armando,Estevez, Angel Ojeda,Fleming, Fraser F.
supporting information, p. 1602 - 1605 (2015/03/04)
Alkyl sulfinates function as formal nucleophiles in Mannich-type reactions to give sulfonyl formamides, which are readily dehydrated to the corresponding sulfonylmethyl isonitriles. The efficient, two-step synthesis provides a general route to sulfonylmethyl isonitriles from readily available methyl sulfinates or thiols. Mechanistic analysis reveals that the unusual nucleophlicity of the alkyl sulfinates arises from the in situ release of sulfinic acids.
Probing the isoprenylcysteine carboxyl methyltransferase (Icmt) binding pocket: Sulfonamide modified farnesyl cysteine (SMFC) analogs as Icmt inhibitors
Majmudar, Jaimeen D.,Hahne, Kalub,Hrycyna, Christine A.,Gibbs, Richard A.
supporting information; experimental part, p. 2616 - 2620 (2011/06/20)
Human isoprenylcysteine carboxyl methyltransferase (hIcmt) is a promising anticancer target as it is important for the post-translational modification of oncogenic Ras proteins. We herein report the synthesis and biochemical activity of 41 farnesyl-cystei
Facile introduction of SH group on aromatic substrates via electrophilic substitution reactions
Becht, Jean-Michel,Wagner, Alain,Mioskowski, Charles
, p. 5758 - 5761 (2007/10/03)
Herein, we describe a mild and efficient two-step procedure to introduce a thiol group on aromatic substrates. First, reaction with an activated sulfoxide leads to an arylsulfonium salt intermediate. Then, two successive β-elimination-based dealkylation reactions afford the desired arylthiols in good to excellent yields.
Dibenzothiepins, phthalans and phthalides from 4-heterosubstituted dibenzothiins
Yus, Miguel,Foubelo, Francisco,Ferrández, José V.
, p. 2083 - 2092 (2007/10/03)
The lithiation of 4-heterosubstituted dibenzothiins 1 (phenoxathiin, phenothiazine and thianthrene) with lithium and a catalytic amount of 4,4′-di-tert-butylbiphenyl (DTBB, 7.5% molar) in THF at temperatures ranging from -90 to -78°C gives the corresponding functionalised organolithium intermediate I, which by reaction with different electrophiles [H2O, D2O, ButCHO, PhCHO, Ph(CH2)2CHO, Me2CO, Et2CO, (CH2)5CO, (CH2)7CO] at the same temperature, followed by hydrolysis, gives the expected functionalised thiols 2. Cyclisation of some thiols 2 under acidic conditions leads to the corresponding seven-membered dibenzo heterocycles 5. In the case of thianthrene 1c, after addition of a carbonyl compound as the first electrophile [MeCHO, ButCHO, Me2CO, Et2CO, (CH2)5CO], the corresponding intermediate II can be lithiated again and react with a second electrophile. Diols 3 are obtained after hydrolysis when a carbonyl compound [ButCHO, PhCHO, Ph(CH2)2CHO, Me2CO, Et2CO, (CH2)5CO] is used as the second electrophile. Acidic cyclisation of diols 3 gives substituted phthalans 6 in almost quantitative yields. Finally, in the case of using carbon dioxide as the second electrophile, phthalides 4 are obtained after acidic hydrolysis.
DTBB-catalyzed lithiation of 4-hetero-substituted dibenzothiins
Yus, Miguel,Foubelo, Francisco,Ferrandez, Jose V.
, p. 726 - 727 (2007/10/03)
The DTBB-catalyzed lithiation of 4-hetero-substituted dibenzothiins (phenoxathiin, phenothiazine, and thianthrene) gives the corresponding functionalized organolithium intermediates, which by reaction with different electrophiles afford the expected funct
The synthesis of new 2,4-diaminofuro[2,3-d]pyrimidines with 5-biphenyl, phenoxyphenyl and tricyclic substitutions as dihydrofolate reductase inhibitors
Gangjee,Dubash,Queener
, p. 935 - 942 (2007/10/03)
Nonclassical 2,4-diamino-5-substituted furo[2,3-d]pyrimidines 4a-i, 5a-b and 7a-f were synthesized as extended aromatic ring appended analogs of previously reported antifolates 1a-b. The extended aromatic system was designed to better interact with a phenylalanine residue (Phe69) of dihydrofolate reductase from the opportunistic pathogen Pneumocystis carinii to afford potent and selective inhibitors of Pneumocystis carinii dihydrofolate reductase. The target compounds were synthesized by nucleophilic displacement of 2,4-diamino-5-(chloromethyl)furo[2,3-d]pyrimidine 3 with the appropriate aromatic amine or thiol. The compounds were evaluated as inhibitors of dihydrofolate reductase from Pneumocystis carinii and Toxoplasma gondii, and their selectivity was determined using rat liver dihydrofolate reductase as the mammalian reference. In the C8-N9 bridged series, compound 4e, with a 3-(2-methoxydibenzofuran)- side chain, exhibited greatest potency and was more than 3 times as selective for Pneumocystis carinii dihydrofolate reductase compared to rat liver dihydrofolate reductase. Compounds 4b and 4c also exhibited selectivity. Compounds in the C8-S9 bridged series showed comparable potencies, and each showed higher selectivity for Pneumocystis carinii dihydrofolate reductase compared to rat liver dihydrofolate reductase.
EFFECT OF MOLECULAR STRUCTURE ON OPTICAL PROPERTIES OF SULFOXIDE SYSTEMS. o-PHENOXYPHENYLSULFINYLACETIC ACIDS AND SOME OF THEIR DERIVATIVES. PART II
Janczewski, Marian,Jablonska-Pikus, Teresa,Kurys, Krystyna,Wilkus, Maria
, p. 91 - 105 (2007/10/02)
The synthesis and principal properties of o-phenoxyphenylthioglycolic as well as o-phenoxyphenylsulfinyl- and sulfonylacetic acids are described.The racemic sulfoxide was resolved by fractional crystallization of its diastereomeric salts with optically active bases.The configurations of the enantiomers were elucidated.Optical rotatory dispersion of the dextro-rotatory enantiomer, its p-bromo and p-phenylphenacyl esters and amide was determined in the region 300 a, ΔS, ΔH) of racemization of dextrorotatory o-phenoxyphenylsulfinylacetic acid were determined by the classical kinetic methods.
