56329-74-9

Basic information

• Product Name: 3,3′-(phenylazanediyl)dipropanehydrazide
• Synonyms: 3,3′-(phenylazanediyl)dipropanehydrazide
• CAS NO: 56329-74-9
• Molecular Weight: 265.315
• Mol File: 56329-74-9.mol

Chemical Properties

• CAS DataBase Reference: 3,3′-(phenylazanediyl)dipropanehydrazide(CAS DataBase Reference)
• NIST Chemistry Reference: 3,3′-(phenylazanediyl)dipropanehydrazide(56329-74-9)
• EPA Substance Registry System: 3,3′-(phenylazanediyl)dipropanehydrazide(56329-74-9)

Safety Data

• Hazardous Substances Data: 56329-74-9(Hazardous Substances Data)

Upstream product

• 61793-99-5 3,3'-phenylimino-di-propionic acid diethyl ester 
• 62-53-3 aniline 
• 53733-94-1 methyl 3-[(3-methoxy-3-oxopropyl)anilino]propanoate 

Downstream Products

• 1071781-21-9 5-(2-{[2-(2-thioxo-2,3-dihydro-1,3,4-oxadiazol-5-yl)ethyl]anilino}ethyl)-2,3-dihydro-1,3,4-oxadiazole-2-thione 
• 1071781-13-9 N-phenyl-2-[3-({3-[2-(anilinocarbonyl)hydrazino]-3-oxopropyl}anilino)propanoyl]-1-hydrazino-carboxamide 
• 1071781-15-1 N-phenyl-2-[3-({3-[2-(anilinothiocarbonyl)hydrazino]-3-oxopropyl}anilino)propanoyl]-1-hydrazino-carbothioamide 
• 1071781-11-7 1-(3,5-dimethyl-1H-1-pyrazolyl)-3-[3-(3,5-dimethyl-1H-1-pyrazolyl)-3-oxopropylanilino]-1-propanone 
• 4182-45-0 N,N-bis-(2-amino-ethyl)-aniline 
• 1071781-19-5 4-phenyl-3-(2-{[2-(4-phenyl-5-thioxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)ethyl]anilino}ethyl)-4,5-dihydro-1H-1,2,4-triazol-5-thione 

Relevant articles and documents

Synthesis and quantitative structure-activity relationship of imidazotetrazine prodrugs with activity independent of O6-methylguanine-DNA- methyltransferase, DNA mismatch repair, and p53

The antitumor prodrug temozolomide is compromised by its dependence for activity on DNA mismatch repair (MMR) and the repair of the chemosensitive DNA lesion, O6-methylguanine (O6-MeG), by O6-methylguanine-DNA-methyltransferase (E.C. 2.1.1.63, MGMT). Tumor response is also dependent on wild-type p53. Novel 3-(2-anilinoethyl)-substituted imidazotetrazines are reported that have activity independent of MGMT, MMR, and p53. This is achieved through a switch of mechanism so that bioactivity derives from imidazotetrazine-generated arylaziridinium ions that principally modify guanine-N7 sites on DNA. Mono- and bifunctional analogues are reported, and a quantitative structure-activity relationship (QSAR) study identified the p-tolyl-substituted bifunctional congener as optimized for potency, MGMT-independence, and MMR-independence. NCI60 data show the tumor cell response is distinct from other imidazotetrazines and DNA-guanine-N7 active agents such as nitrogen mustards and cisplatin. The new imidazotetrazine compounds are promising agents for further development, and their improved in vitro activity validates the principles on which they were designed.

Synthesis and characterization of N-substitutional ethylenediamine derivatives

N-Substituted and N,N-disubstituted ethylenediamine derivatives were prepared rapidly in aqueous conditions from 30 to 76 % yields, respectively, on a multi-gram scale starting from inexpensive and commercially available starting materials. The steps involved Michael addition, hydrazinolysis and Curtius rearrangements. The highlight of this method lies on its convenience and economy in accessing these intermediates.

AMINOALYL-IMIDAZOTETRAZINES FOR TREATMENT OF CANCER

The present invention relates to imidazotetrazines of Formula (I) and their use in the treatment of cancer.