1007559-32-1

Basic information

• Product Name: C₂₁H₁₉NO₅
• Synonyms: C₂₁H₁₉NO₅
• CAS NO: 1007559-32-1
• Molecular Weight: 365.386
• Mol File: 1007559-32-1.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: C₂₁H₁₉NO₅(CAS DataBase Reference)
• NIST Chemistry Reference: C₂₁H₁₉NO₅(1007559-32-1)
• EPA Substance Registry System: C₂₁H₁₉NO₅(1007559-32-1)

Safety Data

• Hazardous Substances Data: 1007559-32-1(Hazardous Substances Data)

Upstream product

• 116569-09-6 5-Hydroxyisatin 
• 39755-95-8 5-methoxyisatine 
• 1007559-33-2 C₃₀H₂₉NO₈ 

Downstream Products

• 1007559-34-3 C₂₁H₁₈INO₅ 

Relevant articles and documents

Streamlined Total Synthesis of Uncialamycin and Its Application to the Synthesis of Designed Analogues for Biological Investigations

From the enediyne class of antitumor antibiotics, uncialamycin is among the rarest and most potent, yet one of the structurally simpler, making it attractive for chemical synthesis and potential applications in biology and medicine. In this article we describe a streamlined and practical enantioselective total synthesis of uncialamycin that is amenable to the synthesis of novel analogues and renders the natural product readily available for biological and drug development studies. Starting from hydroxy- or methoxyisatin, the synthesis features a Noyori enantioselective reduction, a Yamaguchi acetylide-pyridinium coupling, a stereoselective acetylide-aldehyde cyclization, and a newly developed annulation reaction that allows efficient coupling of a cyanophthalide and a p-methoxy semiquinone aminal to forge the anthraquinone moiety of the molecule. Overall, the developed streamlined synthesis proceeds in 22 linear steps (14 chromatographic separations) and 11% overall yield. The developed synthetic strategies and technologies were applied to the synthesis of a series of designed uncialamycin analogues equipped with suitable functional groups for conjugation to antibodies and other delivery systems. Biological evaluation of a select number of these analogues led to the identification of compounds with low picomolar potencies against certain cancer cell lines. These compounds and others like them may serve as powerful payloads for the development of antibody drug conjugates (ADCs) intended for personalized targeted cancer therapy.

Asymmetric synthesis and biological properties of uncialamycin and 26-epi-uncialamycin

(Chemical Equation Presented) The highly potent DNA-cleaving molecule uncialamycin (1) was prepared in an asymmetric total synthesis featuring an enantioselective Noyori reduction. Compound 1 and its C26 epimer exhibit impressive broad-spectrum antibacterial properties and highly potent antitumor activities against a variety of cell lines.