72926-24-0

Basic information

• Product Name: N-(4-Acetyl-4,5-dihydro-5-methyl-5-phenyl-1,3,4-thiadiazol-2-yl)acetamide
• Synonyms: K 858;N-(4-Acetyl-4,5-dihydro-5-methyl-5-phenyl-1,3,4-thiadiazol-2-yl)acetamide
• CAS NO: 72926-24-0
• Molecular Formula: C₁₃H₁₅N₃O₂S
• Molecular Weight: 277
• Mol File: 72926-24-0.mol

Chemical Properties

• Melting Point: 216-217 °C(Solv: ethanol (64-17-5))
• Appearance: white to off-white/
• Density: 1.27±0.1 g/cm3(Predicted)
• Storage Temp.: Store at +4°C
• Solubility: DMSO: ≥20mg/mL
• PKA: 8.61±0.40(Predicted)
• Stability: Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 1 month.
• CAS DataBase Reference: N-(4-Acetyl-4,5-dihydro-5-methyl-5-phenyl-1,3,4-thiadiazol-2-yl)acetamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(4-Acetyl-4,5-dihydro-5-methyl-5-phenyl-1,3,4-thiadiazol-2-yl)acetamide(72926-24-0)
• EPA Substance Registry System: N-(4-Acetyl-4,5-dihydro-5-methyl-5-phenyl-1,3,4-thiadiazol-2-yl)acetamide(72926-24-0)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• WGK Germany: 1
• Hazardous Substances Data: 72926-24-0(Hazardous Substances Data)

Usage

References

1) Nakai et al. (2009), K858, a novel inhibitor of mitotic kinesin Eg5 and antitumor agent, induces cell death in cancer cells; Cancer Res., 69 3901 2) Indorato et al. (2013), STLC-resistant cell lines as tools to classify chemically divergent Eg5 targeting agents according to their mode of action and target specificity; Biochem. Pharmacol.,?86?1441

Upstream product

• 108-24-7 acetic anhydride 
• 132121-93-8 [(1-aza-2-phenylprop-1-enyl)amino]aminomethane-1-thione 
• 2302-93-4 acetophenonethiosemicarbazone 

Downstream Products

• 72926-06-8 1-(5-amino-2-methyl-2-phenyl-1,3,4-thiadiazol-3(2H)-yl)-ethan-1-one 

Relevant articles and documents

Crystal structure of the Eg5 - K858 complex and implications for structure-based design of thiadiazole-containing inhibitors

The thiadiazole scaffold is an important core moiety in a variety of clinical drug candidates targeting a range of diseases. For example, the 2,4,5-substituted 1,3,4-thiadiazole scaffold is present in a lead compound and at least two clinical candidates t

M-STAGE KINESIN INHIBITOR

A mitotic kinesin Eg5 inhibitor which comprises a thiadiazoline derivative represented by the general formula (I) or a pharmacologically acceptable salt thereof as an active ingredient: [wherein R1 represents a hydrogen atom and the like, R2 represents a hydrogen atom, -C(=W)R6 (wherein W represents an oxygen atom or a sulfur atom, and R6 represents substituted or unsubstituted lower alkyl and the like) and the like, R3 represents -C(=Z)R19 (wherein Z represents an oxygen atom or a sulfur atom, and R19 represents substituted or unsubstituted lower alkyl and the like) and the like, R4 represents substituted or unsubstituted lower alkyl and the like, and R5 represents substituted or unsubstituted aryl and the like] and the like are provided.

THIADIAZOLINE DERIVATIVE

(wherein R1 and R4 are the same or different and each represents a hydrogen atom, substituted or unsubstituted lower alkyl, substituted or unsubstituted lower alkynyl, substituted or unsubstituted lower alkenyl, or the like; R5 represents a substituted or unsubstituted heterocyclic group, substituted or unsubstituted aryl, or the like; R2 represents -C(-W)R6 or the like; R3 represents a hydrogen atom, -C(=WA)R6A, or the like) Antitumor agents which comprises a thiadiazoline derivative represented by the aforementioned general formula (I) or a pharmacologically acceptable salt thereof as an active ingredient are provided.

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.