<b>Sulfamoyl Chloride, Sulfamides and Sulfimide</b>

Cohen, Elliott; Klarberg, Betty.

doi:10.1021/ja00869a044

Cited by 31 publications

(21 citation statements)

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“…13 In order to avoid producing a N 1 ,N 3 -and N 1 ,O 4 -disubstituted TTDDs mixture, an unambiguous synthetic pathway was planned for the preparation of the newly designed TTDDs 5a-m. Thus, we chose 3-substituted TTDD 4 as the starting material, which was prepared from methyl 3-amino-2-thiophene carboxylate 2 according to the Cohen and Klarberg procedure, 14 but with an improvement by one-pot reaction. In brief, to an anhydrous toluene solution of the compound 2, N-benzylsulfamoyl chloride 1 dissolved in toluene was added dropwise at room temperature.…”

Section: Chemistrymentioning

confidence: 99%

Synthesis and anti-HIV evaluation of novel 1,3-disubstituted thieno[3,2-c][1,2,6]thiadiazin-4(3H)-one 2,2-dioxides(TTDDs)

Lin

Liu

Yan

et al. 2008

Bioorganic & Medicinal Chemistry

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A series of novel 1,3-disubstituted thieno[3,2-c] [1,2,6]thiadiazin-4(3H)-one 2,2-dioxides (TTDDs), designed as non-nucleoside reverse transcriptase inhibitors (NNRTIs), was synthesized, structurally confirmed by spectral analysis and evaluated for their anti-HIV-1 activities by inhibition of HIV-1(IIIB)-induced cytopathogenicity in MT-4 cell culture. The results showed that TTDD analogues exhibited marked potency as anti-HIV-1 agents. The most active and selective compound was 1-(3-cyano)benzyl-3-benzyl-thieno[3,2-c][1,2,6]thiadiazin-4(3H)-one 2,2-dioxide (5f) with a 50% effective concentration (EC(50)) of 4.0 microM and a selectivity index (SI) of >76. The structure-activity relationship (SAR) is discussed.

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Section: Chemistrymentioning

confidence: 99%

Synthesis and anti-HIV evaluation of novel 1,3-disubstituted thieno[3,2-c][1,2,6]thiadiazin-4(3H)-one 2,2-dioxides(TTDDs)

Lin

Liu

Yan

et al. 2008

Bioorganic & Medicinal Chemistry

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“…Cermelli 748 Vol. 41 The N-3-monosubstituted 2,1,3-benzothiadiazines (11 -15) were obtained following the Cohen and Klarberg procedure [18] starting from the appropriate methyl 2aminobenzoate and sulfamoyl chloride. The use of sodium methoxide instead of 6 N NaOH for the cyclization of the intermediate N-sulfamoylaminobenzoates improves yields (Scheme 3).…”

Section: Chemistrymentioning

confidence: 99%

Synthesis and antiviral activity of new benzothiadiazine dioxide derivatives

Tait

Luppi

Cermelli

2004

Journal of Heterocyclic Chem

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A series of 2,1,3-and 1,2,4-benzothiadiazine derivatives were synthesized by alkylation via Mitsunobu reaction and evaluated for their antiviral activity against ADV, HHV-6, Cox-B5 and H-CMV. Most of them were active at micromolar level against one or more viral strains. All the molecules studied are poorly cytotoxic (maximum non toxic concentrations were >25µM), except one compound that presents a higher cytotoxicity (maximum non toxic concentration was 6 µM).

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“…The benzothiadiazine dioxide ring was obtained in two steps following the Cohen and Klarberg procedure 13 starting from methyl anthranylate and sulfamoyl chloride.…”

Section: Chemistrymentioning

confidence: 99%

“…The structures of all new compounds were elucidated according to analytical and spectroscopic data (see Experimental Section). Unequivocal assignment of all chemical shifts ( 1 H and 13 C NMR) was done using bidimensional experiments such as COSY or HMQC for one-bond correlation. The site of glycosylation was determined from sequences of HMBC for long distance proton/carbon correlation experiments.…”

Section: Chemistrymentioning

confidence: 99%

Novel Potential Agents for Human Cytomegalovirus Infection: Synthesis and Antiviral Activity Evaluation of Benzothiadiazine Dioxide Acyclonucleosides

et al. 1999

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The first acyclonucleosides based on the benzothiadiazine dioxide system were synthesized following the silylation procedure. Several acyclic moieties, including acetoxyethoxymethyl, benzyloxymethyl, and propargyloxymethyl groups, were introduced. Two synthetic strategies were designed to selectively obtain the N-1 or N-3 derivatives. Lipase-mediated deacylation was used for the deprotection of the acyclonucleosides. Some of the benzothiadiazine dioxide acyclonucleosides, in particular 16, proved active against human cytomegalovirus (CMV) at concentrations slightly higher than that found for ganciclovir [50% inhibitory concentration (IC50) = 3. 5-3.7 micrograms/mL, cytotoxicity (CC50) >/= 40 micrograms/mL, MCC = 20 micrograms/mL]. Additionally, compound 16 inhibited the replication of human immunodeficiency virus type 1 (HIV-1) and HIV-2 in CEM cells at concentrations that were 5-fold lower than its cytotoxic concentration.

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Sulfamoyl Chloride, Sulfamides and Sulfimide

Cited by 31 publications

References 0 publications

Synthesis and anti-HIV evaluation of novel 1,3-disubstituted thieno[3,2-c][1,2,6]thiadiazin-4(3H)-one 2,2-dioxides(TTDDs)

Synthesis and anti-HIV evaluation of novel 1,3-disubstituted thieno[3,2-c][1,2,6]thiadiazin-4(3H)-one 2,2-dioxides(TTDDs)

Synthesis and antiviral activity of new benzothiadiazine dioxide derivatives

Novel Potential Agents for Human Cytomegalovirus Infection: Synthesis and Antiviral Activity Evaluation of Benzothiadiazine Dioxide Acyclonucleosides

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