124412-57-3

Basic information

• Product Name: dynemicin A
• Synonyms: dynemicin A;(1S,4R,4aR,14S,14aS)-1,4,4a,7,12,13,14,14a-Octahydro-6,8,11-trihydroxy-3-methoxy-1-methyl-7,12-dioxo-4a,14a-epoxy-4,14-(3-hexene-1,5-diyne-1,6-diyl)naphtho[2,3-c]phenanthridine-2-carboxylic acid;Dynemicin
• CAS NO: 124412-57-3
• Molecular Formula: C₃₀H₁₉NO₉
• Molecular Weight: 537.478
• Mol File: 124412-57-3.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 897.7°Cat760mmHg
• Flash Point: 496.7°C
• Appearance: /
• Density: 1.79g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.845
• CAS DataBase Reference: dynemicin A(CAS DataBase Reference)
• NIST Chemistry Reference: dynemicin A(124412-57-3)
• EPA Substance Registry System: dynemicin A(124412-57-3)

Safety Data

• Hazardous Substances Data: 124412-57-3(Hazardous Substances Data)

Usage

General Description

Dynemicin A is a natural product derived from the bacterium Micromonospora chersina and is known for its potent anticancer properties. It belongs to the enediyne class of compounds, which are characterized by their unique chemical structure and ability to cause DNA damage in targeted cancer cells. Dynemicin A has shown promising results in preclinical studies, demonstrating its ability to effectively inhibit the growth of various cancer cell lines, including multidrug-resistant tumors. Its mechanism of action involves the formation of highly reactive intermediates that directly attack and cleave the DNA strands within cancer cells, leading to their destruction. Due to its impressive anticancer potential, dynemicin A has attracted attention as a potential drug candidate for the treatment of a wide range of cancers.

InChI:InChI=1/C30H19NO9/c1-12-19(28(37)38)27(39-2)13-7-5-3-4-6-8-18-29(12)30(13,40-29)14-11-17(34)22-23(24(14)31-18)26(36)21-16(33)10-9-15(32)20(21)25(22)35/h3-4,9-13,18,31-34H,1-2H3,(H,37,38)/b4-3-/t12-,13+,18-,29-,30+/m0/s1

Upstream product

• 191018-07-2 C₃₅H₄₁NO₇Si 
• 158818-82-7 C₃₆H₄₃NO₈Si 
• 158818-83-8 C₃₁H₃₅NO₅Si 
• 191018-22-1 C₄₈H₆₅NO₉Si₄ 
• 165254-61-5 4,7-bis(trimethylsiloxy)phthalide 
• 177036-31-6 4,7-dihydroxyisobenzofuran-1(3H)-one 

Downstream Products

• 124425-50-9 dynemycin A triacetate 

Relevant articles and documents

A convergent synthetic route to (+)-dynemicin a and analogs of wide structural variability

An enantioselective synthetic route to (+)-dynemicin A (1) is described that involves as the key and final step the Diels-Alder cycloaddition of the quinone imine 6 with the isobenzofuran 107 followed by an oxidative workup to provide (+)-1 in 40% yield. The synthetic route begins with the condensation of (-)-menthyl acetoacetate and trans-ethyl crotonate to form the crystalline cyclohexanedione 14, which is then transformed to the enantiomerically pure quinone imine 6 in 23 steps with an average yield of 85% and an overall yield of 2-3%. Key features of this sequence include the coupling of the enol triflate 11 and the arylboronic acid 10 (90%), the thermal deprotection/internal amidation of the coupling product 18 (84%), the use of 2-chloropyridine as an economical alternative to 2,6-di-tert-butylpyridine to promote the reaction of the quinolone 9 and triflic anhydride (85%), the highly stereoselective addition of the (Z)-enediyne 31 to the quinoline 61 (89%), intramolecular acetylide addition within the acetylenic ketone 66 (94%), and oxidation of the phenol 76 with iodosobenzene to afford the quinone imine precursor 77 in 89% yield. Both the quinone imine and isobenzofuran components of the final coupling reaction can be varied, thus providing an ideal route for the preparation of a wide variety of dynemicin analogs.