28898-88-6

Upstream product

• 2002-03-1 2-amino-5-phenyl-1,3,4-thiadiazole 
• 75-36-5 acetyl chloride 
• 114352-64-6 4-acetyl-1-benzoyl thiosemicarbazide 
• 5351-66-6 benzoyl thiosemicarbazide 
• 108-24-7 acetic anhydride 
• 96133-99-2 C₁₀H₁₃N₃OS 
• 78968-48-6 2,4-dioxopentane 1-amino-2-thiobenzamidoguanidine monohydrazone 
• 5333-86-8 ethyl benzimidate hydrochloride 
• 1627-73-2 1-benzylidene thiosemicarbazide 
• 613-94-5 benzoic acid hydrazide 
• 1663-61-2 triethoxymethylbenzene 
• 100-52-7 benzaldehyde 
• 98-88-4 benzoyl chloride 
• 942-91-6 Carboxymethyl dithiobenzoate 

Downstream Products

• 91265-79-1 2-(ethylamino)-5-phenyl-1,3,4-thiadiazole 
• 91265-81-5 anhydro-2-phenyl-6,8-diethyl-5-hydroxy-7-oxo-1,3,4-thiadiazolo<3,2-a>pyrimidinium hydroxide 
• 2002-03-1 2-amino-5-phenyl-1,3,4-thiadiazole 
• 14537-59-8 2-(Acetylmethylamino)-5-phenyl-Δ²-1,3,4-thiadiazole 
• 3357-38-8 2-(Acetylimino)-3-methyl-5-phenyl-Δ⁴-1,3,4-thiadiazoline 

Relevant academic research and scientific papers

Synthesis and pharmacological screening of a large library of 1,3,4-thiadiazolines as innovative therapeutic tools for the treatment of prostate cancer and melanoma

Antimitotic agents are widely used in cancer chemotherapy but the numerous side effects and the onset of resistance limit their clinical efficacy. Therefore, with the purpose of discovering more selective and efficient anticancer agents to be administered alone or in combination with traditional drugs, we synthesized a large library of 1,3,4-thiadiazoline analogues, maintaining the pharmacophoric structure of an antiproliferative compound known as K858: this is a new inhibitor of kinesin Eg5, able to induce the mitotic arrest in colorectal cancer cells and in xenograft ovarian cancer cells. We screened 103 compounds to assess their antiproliferative activity on PC3 prostate cancer cell line. Two derivatives, compounds 32 (corresponding to K858) and 33, have shown to be the most effective against prostate tumor cells and also towards two melanoma cell lines (SK-MEL-5 and SK-MEL-28) at low micromolar concentrations, confirming the pharmacological activity of this scaffold and revealing the potential role of 1,3,4-thiadiazolines in the management of cancer.

Sulfamic acid-mediated, efficient, one-pot synthesis of novel 5-substituted 1,3,4-thiadiazol-2-ylcarbamoyl aliphatic amide acid derivatives and facile synthesis of cyclic amides

Convenient and efficient one-pot syntheses of 5-substituted-1,3,4- thiadiazol-2- ylcarbamoyl aliphatic amide acid derivatives were described and developed using sulfamic acid catalyst. Thiosemicarbazide and substituted triethylorthoester and cyclic/alicyc

Derives de la dihydro-2,4 triazole-1,2,4 thione-3 et de l'amino-2 thiadiazole-1,3,4 a partir de nouvelles thiosemicarbazones d'esters

A new general synthesis of 4,5-disubstituted 2,4-dihydro-1,2,3-triazole-3-thiones is proposed.These heterocycles are obtained by the action of primary amines, aralhydrazines or aroylhydrazines on the thiosemicarbazones of esters.These last compounds are prepared by action of chlorhydrates of iminoesters on thiosemicarbazide in dimethylformamide.These thiosemicarbazones react also with strong acids, acid anhydrides and chlorides; by thermolysis and they give 2-amino-1,3,4-thiadiazole derivatives.Also, two derivatives of 1,2,4-triazolo-1,3,4-thiadiazole have been prepared.

Stereoselective S-Oxidation of 5-Substituted 4-Acetyl-Δ2-1,3,4-thiadiazolines: X-Ray Crystal Structure of 4-Acetyl-2-acetylamino-5-methyl-5-phenyl-Δ2-1,3,4-thiadiazoline 1-Oxide

N.m.r. spectroscopy and X-ray crystallography show that oxidation of 5-substituted 4-acetyl-2-acetylamino-Δ2-1,3,4-thiadiazolines with m-chloroperbenzoic acid gives the corresponding Δ2-1,3,4-thiadiazoline 1-oxides; the novel reactions of the product (2a) are also described.

THE SYNTHESIS AND CYCLISATIOM OF THIOACYLATED DIAMINOGUANIDINES

The thiobenzoylation of 1,2-diaminoguanidine yields 1-amino-2-thioaroylamidoguanidines which are isolable as their stable hydrazones.They are unaffected by alkalis, but are cyclised by mineral acids, with loss of ammonia, to hydrazones of 2-aryl-5-hydrazino-1,3,4-thiadiazoles, or with elimination of hydrazine, to the appropriate 2-amino-5-aryl-1,3,4-thiadiazoles.The action of acetic anhydride effects the same ring-closures, yielding the corresponding acetylated products. 1,2-Diamino-3-phenylguanidine undergoes a comparable series of reactions.

Synthesis of 4-Acyl-2-(acylamino)-Δ2-1,3,4-thiadiazolines and 4-Acyl-2-amino-Δ2-1,3,4-thiadiazolines by Acylation of Thiosemicarbazones

Acylation of aldehyde and ketone thiosemicarbazones (2) with acid anhydrides or acid chlorides gave 4-acyl-2-(acylamino)-Δ2-1,3,4-thiadiazolines (3) in good yields.Treatment of 3 with hydrazine hydrate furnished the 2-amino derivatives (4).The 4-methylthiosemicarbazone of benzaldehyde underwent a similar cyclization with acetic anhydride to furnish the corresponding 2-(acetylmethylamino)thiadiazoline.