62236-01-5

Upstream product

• 1627-73-2 1-benzylidene thiosemicarbazide 
• 108-24-7 acetic anhydride 
• 75-36-5 acetyl chloride 
• 100-52-7 benzaldehyde 

Downstream Products

• 72926-10-4 4-Acetyl-2-(acetylmethylamino)-5-phenyl-Δ²-1,3,4-thiadiazoline 
• 5378-58-5 2-(acetylamino)-5-methyl-1,3,4-oxadiazole 
• 28898-88-6 N-(5-phenyl-1,3,4-thiadiazol-2-yl)acetamide 
• 1627-73-2 1-benzylidene thiosemicarbazide 
• 72926-26-2 2-(Benzamido)-4-benzoyl-phenyl-Δ²-1,3,4-thiadiazoline 
• 72926-08-0 4-Acetyl-2-(deuterioacetamido)-5-phenyl-Δ²-1,3,4-thiadiazoline 
• 72926-25-1 5-Phenyl-4-propionyl-2-(propionylamino)-Δ²-1,3,4-thiadiazoline 
• 72926-09-1 4-Acetyl-5-phenyl-2-(propionamido)-Δ²-1,3,4-thiadiazoline 
• 72926-11-5 2-(Acetylamino)-5-phenyl-4-propionyl-Δ²-1,3,4-thiadiazoline 
• 72926-07-9 2-Amino-5-phenyl-4-propionyl-Δ²-1,3,4-thiadiazoline 
• 14537-59-8 2-(Acetylmethylamino)-5-phenyl-Δ²-1,3,4-thiadiazole 
• 100-52-7 benzaldehyde 
• 103-30-0 (E)-1,2-diphenyl-ethene 
• 62236-09-3 4-Acetyl-2-amino-5-phenyl-Δ².1,3,4-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.

Cytotoxicity of new 5-phenyl-4,5-dihydro-1,3,4-thiadiazole analogues

A series of 5-phenyl-4,5-dihydro-1,3,4-thiadiazoles were synthesized and their cytotoxicity was examined against four human cancer cell lines, e.g. lung cancer (A549), ovarian cancer (SK-OV-3), skin cancer (SK-MEL- 2), and colon cancer (HCT15). The title compounds were synthesized by condensation of thiosemicarbazide with substituted benzaldehydes, followed by cyclization with acetic anhydrides in good yields. Most of the compounds exhibited significant suppressive activity against the growth of all of the cancer cell lines. The 4-hydroxy analogue of 5-phenyl-4,5-dihydro-1,3,4-thiadiazole (2h) was most active in the inhibition of growth of the SK-MEL-2 cell line, with an IC 50 value of 4.27 μg/ml; followed by compound 2a (IC50 5.16 μg/ml). The compounds 2j, 2h, and 2b, bearing 3-methoxy-4-hydroxy-, 4-hydroxy- and 4-methyl substituents in the C-5 phenyl ring respectively, exhibited the highest activity against the SK-OV-3 (IC50 7.35 μg/ml), HCT15 (IC50 8.25 μg/ml) and A549 (IC509.40 μg/ml) cell lines, respectively. A structure-activity relationship study revealed that an optimal electron density on the C-5 phenyl ring of 1,3,4-thiadiazoles is crucial for their cytotoxic activity against the human cancer cell lines used in the present study.

SYNTHESIS AND PROPERTIES OF 5-FURYL(ARYL)-Δ2-1,2,4-TRIAZOLINES AND -Δ2-1,3,4-THIADIAZOLINES. MOLECULAR AND CRYSTAL STRUCTURE OF 2-ACETYLAMINO-5-PHENYL-Δ2-1,3,4-THIADIAZOLINE

We show that upon acylation of arylidene amidrazones of 5-nitro-2-furancarboxylic acid, 3-(5-nitro-2-furyl)-Δ2-1,2,4-triazolines or 5-(5-nitro-2-furyl)-1,2,4-triazole are formed (depending on the structure of the arylidene moiety). Δ2/sup

4-Acyl-2-acylamino-4,5-dihydro-1,3,4-thiadiazoles by Acylation of Thiosemicarbazones

Thiosemicarbazones and acid anhydrides or halides react to 4-acyl-2-acylamino-4,5-dihydro-1,3,4-thiadiazoles (2a-2v) in high yields. 3-Acyl-2-amino-4,5-dihydro-1,3,4-thiadiazoles 5 are proved as intermediates in this conversion.In special cases they can b

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.