The Reaction of Diazonium Salts on Sodium Alkyl Dithiocarbamates

Clifford, A. M.; Lichty, J. G.

doi:10.1021/ja01342a045

Cited by 45 publications

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“…Dialkyl-substituted dithiocarbamate analogues were prepared by the one-step reaction of secondary amine with carbon disulfide in sodium hydroxide and methanol [33] (see Scheme 1). The mixture was heated to 40 °C and stirred well for 30–120 min, and the methanol was then removed by distillation.…”

Section: Methodsmentioning

confidence: 99%

A novel dithiocarbamate analogue with potentially decreased ALDH inhibition has copper-dependent proteasome-inhibitory and apoptosis-inducing activity in human breast cancer cells

et al. 2011

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Dithiocarbamates are a class of sulfur-based metal-chelating compounds with various applications in medicine. We reported previously that certain members of dithiocarbamates, such as diethyldithiocarbamate, disulfiram (DSF) and pyrrolidine dithiocarbamate (PDTC), were able to bind with tumor cellular copper to inhibit tumor growth through the inhibition of proteasome activity and induction of cancer cell apoptosis. Since the DSF is an irreversible inhibitor of aldehyde dehydrogenase (ALDH), its ALDH-inhibitory activity might potentially affect its usefulness as an anti-cancer drug. For the purpose of selecting potent anti-cancer compounds that are not ALDH inhibitors and mapping out preliminary structure–activity relationship trends for these novel compounds, we synthesized a series of PDTC analogues and chose three novel compounds to study their ALDH-inhibitory activity, proteasome-inhibitory activity as well as the cancer cell apoptosis-inducing activity. The results showed that compared to DSF, compound 9 has less ALDH inhibition activity, and the in vitro results also proved the positive effects of 9-Cu in proteasome inhibition and apoptosis induction in breast cancer cells, suggesting that 9 as a lead compound could be developed into a novel proteasome inhibitor anti-cancer drug.

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Section: Methodsmentioning

confidence: 99%

A novel dithiocarbamate analogue with potentially decreased ALDH inhibition has copper-dependent proteasome-inhibitory and apoptosis-inducing activity in human breast cancer cells

et al. 2011

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“…4-Nitrophenyl NN-dimethyldithiocarbamate was prepared by the method of Clifford & Lichty (1932) [Found: C,45.2;H,4.0;N,11.3;S,26.2. Calc.…”

Section: Methodsmentioning

confidence: 99%

Studies on the interaction between disulfiram and sheep liver cytoplasmic aldehyde dehydrogenase

Kitson¹

1978

Biochemical Journal

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The effect of disulfiram, [1-14C]disulfiram and some other thiol reagents on the activity of cytoplasmic aldehyde dehydrogenase from sheep liver was studied. The results are consistent with a rapid covalent interaction between disulfiram and the enzyme, and inconsistent with the notion that disulfiram is a reversible competitive inhibitor of cytoplasmic aldehyde dehydrogenase. There is a non-linear relationship between loss of about 90% of the enzyme activity and amount of disulfiram added; possible reasons for this are discussed. The remaining approx. 10% of activity is relatively insensitive to disulfiram. It is found that modification of only a small number of groups (one to two) per tetrameric enzyme molecule is responsible for the observed loss of activity. The dehydrogenase activity of the enzyme is affected more severely by disulfiram than is the esterase activity. Negatively charged thiol reagents have little or no effect on cytoplasmic aldehyde dehydrogenase. 2,2'-Dithiodipyridine is an activator of the enzyme.

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“…No desired product was detected when other metal salts such as Pd(OAc) 2 , PdCl 2 , or FeCl 3 were employed as catalysts (entries 8-10). Then, various bases such as Cs 2 CO 3 , KOH, tBuOK, and NEt 3 were screened (entries [11][12][13][14]. The results revealed that Cs 2 CO 3 was the most efficient, giving the desired product in 65 % yield (entry 11).…”

Section: Resultsmentioning

confidence: 99%

“…Moreover, they can be used as linkers in solidphase organic synthesis, [7] protecting groups in peptide synthesis, [8] and have recently been used in the synthesis of ionic liquids. [10] A couple of metal-free procedures involve the reaction of the sodium salt of dithiocarbamic acid with diazonium chloride [11] and diaryl diazonium salts in the presence of hypervalent iodine, [12] the reaction of certain organometallic reagents with tetramethyllithium disulfide, [13] coupling of sodium dithiocarbamates with aryl iodides or halobenzene. The most commonly used method is the reaction of amines with thiophosgene or isothiocyanates.…”

Section: Introductionmentioning

confidence: 99%

“…The most commonly used method is the reaction of amines with thiophosgene or isothiocyanates. [10] A couple of metal-free procedures involve the reaction of the sodium salt of dithiocarbamic acid with diazonium chloride [11] and diaryl diazonium salts in the presence of hypervalent iodine, [12] the reaction of certain organometallic reagents with tetramethyllithium disulfide, [13] coupling of sodium dithiocarbamates with aryl iodides or halobenzene. [14] Other protocols such as onepot three component reactions of amines, carbon disulfide with electrophiles including alkyl halides [15] or aryl halides, [16] aryl diazonium fluoroborates, [17] pentafluorobenzonitriles, [18] or benzene boronic acid [19] were reported.…”

Section: Introductionmentioning

confidence: 99%

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Copper‐Catalyzed S‐Arylation Starting from Arylboronic Acids and Tetraalkylthiuram Disulfide

Dong

2018

Eur J Org Chem

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A convenient and useful protocol for the synthesis of diverse S‐aryl dithiocarbamates was studied. Starting from arylboronic acid and tetraalkylthiuram disulfide, copper‐catalyzed C–S coupling proceeds smoothly to give the desired S‐aryl dithiocarbamates in good to excellent yields. The broad substrate scope, short reaction time, easy performance, cheap substrates, and nice yields make this approach attractive, showing its practical synthetic value for the preparation of some biologically or pharmaceutically active compounds.

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The Reaction of Diazonium Salts on Sodium Alkyl Dithiocarbamates

Cited by 45 publications

References 0 publications

A novel dithiocarbamate analogue with potentially decreased ALDH inhibition has copper-dependent proteasome-inhibitory and apoptosis-inducing activity in human breast cancer cells

A novel dithiocarbamate analogue with potentially decreased ALDH inhibition has copper-dependent proteasome-inhibitory and apoptosis-inducing activity in human breast cancer cells

Studies on the interaction between disulfiram and sheep liver cytoplasmic aldehyde dehydrogenase

Copper‐Catalyzed S‐Arylation Starting from Arylboronic Acids and Tetraalkylthiuram Disulfide

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