66082-27-7

Usage

Uses

Used in Pharmaceutical Industry:
Saframycin A is used as an anticancer agent for its ability to effectively disrupt the growth and proliferation of cancer cells. It targets the topoisomerase II enzyme, which is essential for DNA replication and repair, thereby inhibiting cancer cell division and potentially leading to cell death.
Used in Antibacterial Applications:
In the field of antibacterial therapy, saframycin A is utilized as an antibiotic due to its potent activity against bacteria. By intercalating into bacterial DNA and inhibiting topoisomerase II, it disrupts the bacteria's ability to replicate and repair their DNA, leading to bacterial growth inhibition and potentially eradication.
These applications highlight the versatility of saframycin A in both cancer treatment and bacterial infection management, underscoring its potential as a valuable asset in the medical and pharmaceutical sectors.

InChI:InChI=1/C29H30N4O8/c1-11-23(35)14-8-17-22-21-15(24(36)12(2)28(41-6)26(21)38)7-16(32(22)4)18(9-30)33(17)19(10-31-29(39)13(3)34)20(14)25(37)27(11)40-5/h16-19,22H,7-8,10H2,1-6H3,(H,31,39)

Upstream product

• 1310875-44-5 C₃₇H₄₄BrN₃O₁₀ 
• 1310875-45-6 C₂₄H₂₈BrN₃O₅ 
• 1310875-46-7 C₂₉H₃₆BrN₃O₇ 
• 1310875-47-8 C₃₀H₃₈BrN₃O₇ 
• 1310875-48-9 C₃₀H₃₉N₃O₇ 
• 1310875-49-0 C₃₁H₄₀N₄O₆ 
• 1310875-50-3 C₂₆H₃₂N₄O₄ 
• 1310875-51-4 C₂₉H₃₄N₄O₆ 
• 1310875-39-8 benzyl ((1R,3S)-8-hydroxy-3-(hydroxymethyl)-7-methoxy-6-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl)methylcarbamate 
• 1310875-40-1 benzyl ((1R,3S)-8-(tert-butyldimethylsilyloxy)-3-((tert-butyldimethylsilyloxy)methyl)-7-methoxy-6-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl)methylcarbamate 
• 1310875-41-2 C₅₅H₈₈BrN₃O₁₀Si₃ 
• 1310875-42-3 C₄₉H₇₄BrN₃O₁₀Si₂ 
• 1310875-43-4 C₄₉H₇₂BrN₃O₁₀Si₂ 
• 686776-27-2 (S)-5-(2-amino-3-hydroxypropyl)-2-methoxy-3-methylphenol 

Downstream Products

• 92569-02-3 (-)-saframycin G 
• 161024-29-9 (+)-5-epi-saframycin G 
• 92569-03-4 (+)-saframycin F 
• 92569-02-3 (-)-saframycin G 
• 92569-02-3 (+)-5-epi-saframycin G 

Relevant academic research and scientific papers

Structure of saframycin R

The structure of saframycin R was determined to be 1 (form I) by the two-dimensional 1H detected heteronuclear correlation experiments (HMQC and HMBC) of its acylated compounds 4a and 4b. (C) 2000 Elsevier Science Ltd.

Chemo-enzymatic Total Syntheses of Jorunnamycin A, Saframycin A, and N-Fmoc Saframycin Y3

The antitumor tetrahydroisoquinoline (THIQ) alkaloids share a common pentacyclic scaffold that is biosynthesized by nonribosomal peptide synthetases involving unique enzymatic Pictet-Spengler cyclizations. Herein we report concise and divergent chemo-enzymatic total syntheses of THIQ alkaloids by merging precise chemical synthesis with in vitro engineered biosynthesis. A recombinant enzyme SfmC responsible for the biosynthesis of saframycin A was adapted for the assembly of these natural products and their derivatives, by optimizing designer substrates compatible with SfmC through chemical synthesis. The appropriately functionalized pentacyclic skeleton were efficiently synthesized by streamlining the linkage between SfmC-catalyzed multistep enzymatic conversions and chemical manipulations of the intermediates to install aminonitrile and N-methyl groups. This approach allowed rapid access to the elaborated pentacyclic skeleton in a single day starting from two simple synthetic substrates without isolation of the intermediates. Further functional group manipulations allowed operationally simple and expeditious syntheses of jorunnamycin A, saframycin A, and N-Fmoc saframycin Y3 that could be versatile and common precursors for the artificial production of other antitumor THIQ alkaloids and their variants.

A stereocontrolled total synthesis of (±)-saframycin A

A thirteen-step total synthesis of (±)-saframycin A from a tricyclic lactam intermediate is described. The key step of this total synthesis is the stereocontrolled construction of a pentacyclic saframycin framework via a modified Pictet-Spengler type cyclization generating a bis-carboxylic acid ester derivative, followed by decarboxylation. The cytotoxicity profiles are also presented.

Asymmetric total synthesis of (-)-saframycin A from l-tyrosine

The asymmetric total synthesis of (-)-saframycin A, a natural antitumor product of the tetrahydroisoquinoline antitumor antibiotics family, has been accomplished by employing l-tyrosine as the starting chiral building block in 24 steps for the longest lin