62236-08-2

Basic information

• Product Name: N-{4-ACETYL-5-[4-(DIMETHYLAMINO)PHENYL]-4,5-DIHYDRO-1,3,4-THIADIAZOL-2-YL}ACETAMIDE
• Synonyms: N-{4-ACETYL-5-[4-(DIMETHYLAMINO)PHENYL]-4,5-DIHYDRO-1,3,4-THIADIAZOL-2-YL}ACETAMIDE;TOSLAB 865147
• CAS NO: 62236-08-2
• Molecular Formula: C₁₄H₁₈N₄O₂S
• Molecular Weight: 306.38
• Mol File: 62236-08-2.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: N-{4-ACETYL-5-[4-(DIMETHYLAMINO)PHENYL]-4,5-DIHYDRO-1,3,4-THIADIAZOL-2-YL}ACETAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: N-{4-ACETYL-5-[4-(DIMETHYLAMINO)PHENYL]-4,5-DIHYDRO-1,3,4-THIADIAZOL-2-YL}ACETAMIDE(62236-08-2)
• EPA Substance Registry System: N-{4-ACETYL-5-[4-(DIMETHYLAMINO)PHENYL]-4,5-DIHYDRO-1,3,4-THIADIAZOL-2-YL}ACETAMIDE(62236-08-2)

Safety Data

• Hazardous Substances Data: 62236-08-2(Hazardous Substances Data)

Upstream product

• 2929-81-9 4-(N,N-dimethylamino)benzaldehyde thiosemicarbazone 
• 108-24-7 acetic anhydride 
• 100-10-7 4-dimethylamino-benzaldehyde 

Downstream Products

• 72926-28-4 1-[5-Amino-2-(4-dimethylamino-phenyl)-[1,3,4]thiadiazol-3-yl]-ethanone 

Relevant articles and documents

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 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.