1454276-30-2

Basic information

• Product Name: ethyl 1-acetylamino-2-phenylazuleno[2,1-b]pyrrole-9-carboxylate
• Synonyms: ethyl 1-acetylamino-2-phenylazuleno[2,1-b]pyrrole-9-carboxylate
• CAS NO: 1454276-30-2
• Molecular Weight: 357.409
• Mol File: 1454276-30-2.mol

Chemical Properties

• CAS DataBase Reference: ethyl 1-acetylamino-2-phenylazuleno[2,1-b]pyrrole-9-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 1-acetylamino-2-phenylazuleno[2,1-b]pyrrole-9-carboxylate(1454276-30-2)
• EPA Substance Registry System: ethyl 1-acetylamino-2-phenylazuleno[2,1-b]pyrrole-9-carboxylate(1454276-30-2)

Safety Data

• Hazardous Substances Data: 1454276-30-2(Hazardous Substances Data)

Upstream product

• 76279-84-0 ethyl 2-acetylamino-3-iodoazulene-1-carboxylate 
• 536-74-3 phenylacetylene 

Relevant articles and documents

Synthesis, cyclization, and evaluation of the anticancer activity against hela S-3 cells of ethyl 2-acetylamino-3-ethynylazulene-1-carboxylates

Reaction of ethyl 2-aminoazulene-1-carboxylate with NIS in CHCl3 gave 2,2'-diamino-3,3'-diethoxycarbonyl-1,1'-biazulene (3) and a terazulene derivative. The coupling of azulenes was catalyzed by acid. Operation of the reaction in the presence of Et3N in CH2Cl2 for 7 min at -7 °C retarded the coupling of the azulene nuclei to give ethyl 2-amino-3-iodoazulene-1-carboxylate (1a) in 95% yield. Sonogashira cross-coupling of ethyl 2-acetylamino-3-iodoazulene-1-carboxylate (1b) gave ethyl 2-acetylamino-3-ethynylazulene-1-carboxylates (5a and 5b) in good yields. Cyclization of ethyl 2-acetylamino-3-phenylethynylazulene-1-carboxylate with Pd-catalyst gave azuleno[2,1-b]pyrrole derivatives. Compounds (3 and 5b) showed potent cytotoxic activity against HeLa S-3 cells (IC50 [μM] : 3: 2.9 ± 0.2, 5b: 13.4 ± 1.1).