Effects of 3-Chloromethylthiochromone-1, 1-dioxide on Nucleic Acid, Protein, and Aerobic and Anaerobic Metabolism of Ehrlich Ascites Tumor Cells

Holshouser, Mark H.; Loeffler, Larry J.; Hall, Iris H.

doi:10.1002/jps.2600710804

Cited by 4 publications

(2 citation statements)

References 33 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…2,3-Dihydro-4 H -1-benzothiopyran-4-ones and their 2-phenyl derivatives (widely cited by the semitrivial names 1-thiochroman-4-ones and 1-thioflavanones), as well as 4 H -1-benzothiopyran-4-ones and their 2-phenyl derivatives (1-thiochromones and 1-thioflavones) are the thio analogues of the naturally occurring chromonoid and flavonoid compounds . Some of these substances, particularly their sulfones, have been shown to display antibacterial, fungicidal, antitumor, 3b, HIV-inhibitor,5d human-cytomegalovirus (HCMV)-protease-inhibitor, serotonin-3-receptor-antagonic, antiallergic, diuretic and antihypertensive, immunosupressive, and weak CNS 11 activities. Despite their interesting pharmacological properties, relatively little has been published on the oxidation chemistry of thiochromonoids and thioflavonoids.…”

Section: Introductionmentioning

confidence: 99%

Chemo- and Diastereoselectivity in the Dimethyldioxirane Oxidation of 2,3-Dihydro-4H-1-benzothiopyran-4-ones and 4H-1-Benzothiopyran-4-ones. Unusual Reactivity of 4H-1-Benzothiopyran-4-one 1-Oxides¹

et al. 2001

View full text Add to dashboard Cite

The oxidation of the 1-thiochromanones 1-3 by dimethyldioxirane (DMD) produced the corresponding sulfoxides 4-6 or sulfones 7-9; their relative amounts depended on the amount of oxidant used. A low diastereoselectivity was observed in the sulfoxidation of the 2-substituted 1-thiochromanones 2 and 3, due to the small steric differentiation during the DMD attack. An unusual reactivity pattern was found in the DMD oxidation of the 1-thiochromones 10-12, in that the sulfoxides 13-15 were more reactive toward the electrophilic oxidizing agent than the corresponding sulfides. The observed anomaly may be explained in terms of transannular stabilization of the transition structure (TS) for the sulfone formation, promoted through favorable conformational effects in the sulfoxide. Higher sulfoxide/sulfone ratios were found in solvents of greater hydrogen bond donor capacity, which is in accordance with the postulated stabilizing effect.

show abstract

Section: Introductionmentioning

confidence: 99%

Chemo- and Diastereoselectivity in the Dimethyldioxirane Oxidation of 2,3-Dihydro-4H-1-benzothiopyran-4-ones and 4H-1-Benzothiopyran-4-ones. Unusual Reactivity of 4H-1-Benzothiopyran-4-one 1-Oxides¹

et al. 2001

View full text Add to dashboard Cite

show abstract

“…2,4 The benzothiopyrans show also pharmacological properties as antibacterials, antiallergics, antitumoral, sedatives, hypoglycemic and hypocholesterolemic; other interests lie in the treatment of AIDS. 2,[5][6][7][8][9] The methods of preparation of benzothiopyrans reported in the literature consist in the cyclocondensation of arylthiopropenes, arylthiopropanoic or arylthioacrylic acids and esters, the cyanoethylation of mercaptocarboxylic acids and the polar cationic [4 + +2] between chloromethylphenylsulfide and styrene or trans -stilbene or phenylacetylene. [10][11][12][13][14][15][16][17] In this work we describe a new one-step synthesis of benzothiopyranic derivatives.It was previously found that the thiomethyl and the sulfonylalkyl groups are able to promote the metallation of the ortho -and α -positions.…”

mentioning

confidence: 99%

A New One-Step Synthesis of Benzothiopyran Derivatives

Cabiddu¹,

Cabiddu²,

Cadoni³

et al. 1998

Synthesis

View full text Add to dashboard Cite

Methylthio)-and (isopropylthio)benzene are useful synthetic intermediates to prepare bimetallated intermediates which, after reaction with α -diketones, lead to benzothiopyranic derivatives in one-step and with good yields.A few benzothiopyranic compounds have been detected in crude oil 2 and in several sulfur rich sediments: 3 the lack of natural availability of this heterocyclic ring makes its de novo synthesis necessary. The importance of these compounds lies in their use in the dye industry and as photoactive agents. 2,4 The benzothiopyrans show also pharmacological properties as antibacterials, antiallergics, antitumoral, sedatives, hypoglycemic and hypocholesterolemic; other interests lie in the treatment of AIDS. 2,5-9The methods of preparation of benzothiopyrans reported in the literature consist in the cyclocondensation of arylthiopropenes, arylthiopropanoic or arylthioacrylic acids and esters, the cyanoethylation of mercaptocarboxylic acids and the polar cationic [4 + +2] between chloromethylphenylsulfide and styrene or trans -stilbene or phenylacetylene. [10][11][12][13][14][15][16][17] In this work we describe a new one-step synthesis of benzothiopyranic derivatives.It was previously found that the thiomethyl and the sulfonylalkyl groups are able to promote the metallation of the ortho -and α -positions. [18][19][20][21] This method allows to prepare sulfur compounds orthoand α -dilithiated by direct bimetallation of alkylaromatic thioethers and sulfones using two molar equivalents of butyllithium. The lithiated intermediates can react with bifunctionalized compounds as esters and acyl halides to give benzo[ b ]thiophenes.Attempts to prepare benzothiopyrans by reaction of diethyloxalate with these dilithiated species were unsuccessful. In fact this compound reacts with only one ester group because the carbonyl carbon of the intermediate ketone is more electrophilic than the ester. 19Now we have successfully performed the synthesis using α -diketones. The bimetallated species obtained from (methylthio)-( 1a ) and (isopropylsulfonyl)arenes ( 1b,c ) were reacted with equimolar amounts of α -diketones in tetrahydrofuran at -80°C. The reaction mixture was allowed to warm up to room temperature with stirring. The benzothiopyran derivatives 3a-f were obtained in good yields (55-65%) (Scheme, Tables 1 and 2), thus showing that both lithiated centres attack the two carbonyl carbons. The reaction was diastereoselective giving only the isomer with the two hydroxy groups in the trans diaxial configuration. The stereochemistry of compounds 3a-f was determined by NOE difference and NOESY experiments.Solutions of butyllithium in hexane were purchased from Aldrich and were analyzed by the Gilman double titration method. 22 Analytical TLC plates and silica gel (230-400 mesh) were purchased from Merck. IR spectra were recorded on a Perkin-Elmer 1310 grating spectrophotometer using NaCl plates. 1 H and 13 C NMR spectra were recorded on a Varian VXR-300 spectrometer. Mass spectra were obtained at 70 eV with a Hewlett-Pac...

show abstract

Inhibition of protein synthesis in neoplastic cells by rhein

S¹,

Paggi²,

Delpino³

et al. 1990

Biochemical Pharmacology

View full text Add to dashboard Cite

Effects of 3-Chloromethylthiochromone-1, 1-dioxide on Nucleic Acid, Protein, and Aerobic and Anaerobic Metabolism of Ehrlich Ascites Tumor Cells

Cited by 4 publications

References 33 publications

Chemo- and Diastereoselectivity in the Dimethyldioxirane Oxidation of 2,3-Dihydro-4H-1-benzothiopyran-4-ones and 4H-1-Benzothiopyran-4-ones. Unusual Reactivity of 4H-1-Benzothiopyran-4-one 1-Oxides¹

Chemo- and Diastereoselectivity in the Dimethyldioxirane Oxidation of 2,3-Dihydro-4H-1-benzothiopyran-4-ones and 4H-1-Benzothiopyran-4-ones. Unusual Reactivity of 4H-1-Benzothiopyran-4-one 1-Oxides¹

A New One-Step Synthesis of Benzothiopyran Derivatives

Inhibition of protein synthesis in neoplastic cells by rhein

Contact Info

Product

Resources

About

Effects of 3-Chloromethylthiochromone-1, 1-dioxide on Nucleic Acid, Protein, and Aerobic and Anaerobic Metabolism of Ehrlich Ascites Tumor Cells

Cited by 4 publications

References 33 publications

Chemo- and Diastereoselectivity in the Dimethyldioxirane Oxidation of 2,3-Dihydro-4H-1-benzothiopyran-4-ones and 4H-1-Benzothiopyran-4-ones. Unusual Reactivity of 4H-1-Benzothiopyran-4-one 1-Oxides1

Chemo- and Diastereoselectivity in the Dimethyldioxirane Oxidation of 2,3-Dihydro-4H-1-benzothiopyran-4-ones and 4H-1-Benzothiopyran-4-ones. Unusual Reactivity of 4H-1-Benzothiopyran-4-one 1-Oxides1

A New One-Step Synthesis of Benzothiopyran Derivatives

Inhibition of protein synthesis in neoplastic cells by rhein

Contact Info

Product

Resources

About

Chemo- and Diastereoselectivity in the Dimethyldioxirane Oxidation of 2,3-Dihydro-4H-1-benzothiopyran-4-ones and 4H-1-Benzothiopyran-4-ones. Unusual Reactivity of 4H-1-Benzothiopyran-4-one 1-Oxides¹

Chemo- and Diastereoselectivity in the Dimethyldioxirane Oxidation of 2,3-Dihydro-4H-1-benzothiopyran-4-ones and 4H-1-Benzothiopyran-4-ones. Unusual Reactivity of 4H-1-Benzothiopyran-4-one 1-Oxides¹