Verfahren zur Darstellung aliphatischer, aromatischer und heterocyclischer Rhodanverbindungen aus Mercaptanen 27. Mitt.: Über organische Rhodanverbindungen

Kottke, K.; Friedrich, Felix; Pohloudek-Fabini, R

doi:10.1002/ardp.19673000704

Cited by 17 publications

(4 citation statements)

References 35 publications

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“…The precipitate was filtered and washed thoroughly with water. [42] 5.1.4 | Synthesis of 4-(3-sulfamoylphenyl)thiosemicarbazide (7) To a solution of hydrazine (5 mmol) in ethanol (10 ml), a suspension of 3-(isothiocyanato)benzenesulfonamide (6) (5 mmol) in ethanol (10 ml) was added dropwise with vigorous stirring and cooling in an ice bath.…”

Section: Discussionmentioning

confidence: 99%

New 1H‐indole‐2,3‐dione 3‐thiosemicarbazones with 3‐sulfamoylphenyl moiety as selective carbonic anhydrase inhibitors

Eraslan-Elma

Akdemir

Berrino

et al. 2022

Archiv der Pharmazie

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1-Methyl/ethyl/benzyl-5-(un)substituted 1H-indole-2,3-diones (2, 3, and 4) were synthesized by reaction of 5-(un)substituted 1H-indole-2,3-diones (1) with methyl iodide, ethyl chloride, and benzyl bromide. (3-Sulfamoylphenyl)isothiocyanate (6) was obtained by the treatment of 3-aminobenzenesulfonamide (5) with thiophosgene. Compound 6 was reacted with hydrazine to yield 4-(3-sulfamoylphenyl) thiosemicarbazide (7). Novel 1-(un)substituted/methyl/ethyl/benzyl-5-(un) substituted 1H-indole-2,3-dione 3-[4-(3-sulfamoylphenyl)thiosemicarbazone] derivatives (8−11) were prepared by condensation of 7 and 1−4. The structures of the synthesized compounds were confirmed by elemental analysis and spectral data. Inhibition of the widely distributed cytosolic off-targets human carbonic anhydrases (hCAs) I and II, and two tumor-associated membrane-bound isoforms (hCAs IX and XII), by 8−11 was investigated. The hCA II inhibitory effects of all tested compoundswere in the subnanomolar to low nanomolar levels (K i = 0.32−83.3 nM), and generally high selectivity for hCA II isoenzyme over hCA I, IX, and XII isoenzymes was observed. The strongest inhibitors of hCA II, 1-benzyl-5-(trifluoromethoxy)substituted 11c (K i = 0.32 nM) and 1-ethyl-5-chloro-substituted 10e (K i = 0.35 nM), were docked within the enzyme active site. Molecular modeling studies with the most effective hCA IX and XII inhibitors were also carried out.

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Section: Discussionmentioning

confidence: 99%

New 1H‐indole‐2,3‐dione 3‐thiosemicarbazones with 3‐sulfamoylphenyl moiety as selective carbonic anhydrase inhibitors

Eraslan-Elma

Akdemir

Berrino

et al. 2022

Archiv der Pharmazie

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“…[1] This reaction is significant due to the fact that organic thiocyanates are not only efficient synthetic precursors for diverse valuable sulphur-containing compounds, but also have important functionality in natural marine sponges and alkaloids. [2] The thiocyano group (-SCN) is a versatile cyano-moiety with diverse convertibility, [3] good leaving capability and bioactivity. [4] Recent experimental reports [5] have outlined how the asymmetric thiocyanation reaction can be effected by cinchona alkaloid systems.…”

Section: Introductionmentioning

confidence: 99%

“…One of the important applications in asymmetric organocatalysis has been in the successful execution of the asymmetric alpha thiocyanation reaction [1] . This reaction is significant due to the fact that organic thiocyanates are not only efficient synthetic precursors for diverse valuable sulphur‐containing compounds, but also have important functionality in natural marine sponges and alkaloids [2] . The thiocyano group (‐SCN) is a versatile cyano‐moiety with diverse convertibility, [3] good leaving capability and bioactivity [4] .…”

Section: Introductionmentioning

confidence: 99%

The “Weak” C−H⋅⋅⋅S Interaction Drives Enantioselectivity in Cinchona Alkaloid Complex Catalyzed Thiocyanation

Banerjee

Vanka

2023

Chemistry An Asian Journal

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The great success of asymmetric organocatalysis has made it one of the most important advancements made in chemistry in the past two decades. A significant achievement in this context is the asymmetric organocatalysis of the thiocyanation reaction. In the current study, computational studies with density functional theory have been done in order to understand an interesting experimental finding: the reversal of enantioselectivity from R to S when the electrophile is changed from β‐keto ester to oxindole for the thiocyanation reaction with the cinchona alkaloid complex catalyst. The calculations reveal an unusual fact – the principal reason for the reversal is the presence of the C−H⋅⋅⋅S noncovalent interaction, which is present only in the major transition states in each of the two nucleophile cases. Only recently has it been realized that the supposedly weak C−H⋅⋅⋅S noncovalent interaction has the properties of a hydrogen bond, and the fact that this interaction is the cause of enantioselectivity has relevance, because of the large number of asymmetric transformations involving the sulphur heteroatom.

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“…(9) The measured parent ion (M+) mass is slightly beyond acceptable error limits due to interference by the 13C isotope peak of the intense (base) M+ - 1 ion; however, the flanking m/e 119 and 117 ions gave the correct accurate masses for the assigned structure. (10) After the studies reported in this paper were concluded our attention was directed to a report by T. Kumagai and T. Mukai [Chem. Lett., 1187Lett., (1975 in which these authors propose the structure 1 for the 30% component isolated from the acetone-sensitized photolysis of tricyclo[3.2.2.02•4]nona-6,8-diene (homobarrelene).…”

mentioning

confidence: 99%

Aryl selenocyanates and aryl thiocyanates: reagents for the preparation of activated esters

Grieco¹,

Yokoyama²,

Williams³

1978

J. Org. Chem.

138

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Verfahren zur Darstellung aliphatischer, aromatischer und heterocyclischer Rhodanverbindungen aus Mercaptanen 27. Mitt.: Über organische Rhodanverbindungen

Cited by 17 publications

References 35 publications

New 1H‐indole‐2,3‐dione 3‐thiosemicarbazones with 3‐sulfamoylphenyl moiety as selective carbonic anhydrase inhibitors

New 1H‐indole‐2,3‐dione 3‐thiosemicarbazones with 3‐sulfamoylphenyl moiety as selective carbonic anhydrase inhibitors

The “Weak” C−H⋅⋅⋅S Interaction Drives Enantioselectivity in Cinchona Alkaloid Complex Catalyzed Thiocyanation

Aryl selenocyanates and aryl thiocyanates: reagents for the preparation of activated esters

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