1227962-62-0

Basic information

• Product Name: Marinopyrrole A
• Synonyms: 1,1'-(4,4',5,5'-Tetrachloro[1,3'-bi-1H-pyrrole]-2,2'-diyl)bis[1-(2-hydroxyphenyl)methanone];Marinopyrrole A(Maritoclax);Maritoclax, (±)-Marinopyrrole A
• CAS NO: 1227962-62-0
• Molecular Formula: C₂₂H₁₂Cl₄N₂O₄
• Molecular Weight: 510.15368
• Mol File: 1227962-62-0.mol

Chemical Properties

• Melting Point: 205-207℃
• Boiling Point: 732.4±60.0 °C(Predicted)
• Appearance: /
• Density: 1.62±0.1 g/cm3(Predicted)
• Solubility: Soluble in DMSO
• PKA: 6.87±0.30(Predicted)
• CAS DataBase Reference: Marinopyrrole A(CAS DataBase Reference)
• NIST Chemistry Reference: Marinopyrrole A(1227962-62-0)
• EPA Substance Registry System: Marinopyrrole A(1227962-62-0)

Safety Data

• Hazardous Substances Data: 1227962-62-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Marinopyrrole A is used as an anticancer agent for its ability to target and inhibit the growth of cancer cells. It has demonstrated efficacy against various types of cancer, making it a valuable asset in the development of novel cancer therapies.
Used in Medical Industry:
Marinopyrrole A is used as an anti-bacterial agent, particularly against methicillin-resistant Staphylococcus aureus (MRSA). Its ability to combat antibiotic-resistant bacteria highlights its potential in addressing the growing issue of bacterial resistance and the need for new antimicrobial agents.

Biological Activity

marinopyrrole a is a selective inhibitor of mcl-1 with ic50 value of 10.1μm [1].marinopyrrole a is a natural product froma species of marine-derived streptomycetes and is reported to be an antagonist of mcl-1. mcl-1 is a member of the anti-apoptotic bcl-2 family, which is a well-validated drug target for cancer treatment. nmr titration experiments show that marinopyrrole a can directly interact with mcl-1. it can prevent bim-bh3 peptides from binding to mcl-1 but not bcl-xl. the cell based assay shows a high selectivity of marinopyrrole a. treatment with marinopyrrole a inhibit the viability of k562 cells transfected with mcl-1 gene with ec50 value of 1.6μm. the selectivity is more than 40-fold greater over the cells transfected with bcl-xl gene. moreover, marinopyrrole a can decreases mcl-1 expression by increasing the cleavage of caspase-3 and parp. marinopyrrole a is also reported to completely restore the sensitivity of multidrug resistant leukemia cells to abt-737 [1].

references

[1] doi k, li r, sung ss, et al. discovery of marinopyrrole a (maritoclax) as a selective mcl-1 antagonist that overcomes abt-737 resistance by binding to and targeting mcl-1 for proteasomal degradation. j biol chem. 2012 mar, 287(13): 10224-35.

Upstream product

• 252932-48-2 3-amino-2-ethoxycarbonylpyrrole 
• 21615-34-9 2-Methoxybenzoyl chloride 
• 579-75-9 2-Methoxybenzoic acid 
• 1305334-94-4 1'H-[1,3'-bipyrrol]-2'-yl(2-methoxyphenyl)methanone 
• 1305334-93-3 ethyl 1'H-1,3'-bipyrrole-2'-carboxylate 
• 1227869-59-1 1'H-1,3'-bipyrrole-2,2'-diylbis[(2-methoxyphenyl)methanone] 
• 1227869-61-5 (4,4′,5,5′-tetrachloro-1′H-[1,3′-bipyrrole]-2,2′-diyl)bis((2-methoxyphenyl)methanone) 

Downstream Products

• 1186308-34-8 C₃₇H₂₆Cl₄N₄O₈ 
• 1305334-97-7 (4,4',5,5'-tetrachloro-1'H-1,3'-bipyrrole-2,2'-diyl)bis((2-acetoxyphenyl)methanone) 

Relevant articles and documents

Exploration of the Bis(thio)urea-Catalyzed Atropselective Synthesis of Marinopyrrole A

The marinopyrroles are a new class of natural products with highly interesting biomedical and structural features. We herein provide a concise, nitrogen-protective-group-free synthesis of marinopyrrole A, constituting the as yet most efficient route. The

MCL-1 MODULATING COMPOSITIONS

The present invention relates to marinopyrrole A derivatives and pyoluteorin derivatives and methods of treatment of disorders associated with misregulation of Mcl-l, e.g., leukemia, lymphoma, multiple myeloma, melanoma, or pancreatic cancer. We describe exemplary compounds, which may be contained in pharmaceutical compositions, and their use as therapeutic agents either alone or in combination with other anti-cancer treatments, e.g., anti-Bcl- 2 agents.

Total synthesis and biological evaluation of marinopyrrole A and analogs

A five-step total synthesis of the antibiotic marinopyrrole A (1) is described. The developed synthetic technology enabled the synthesis of several marinopyrrole A analogs whose antibacterial properties against methicillin-resistant Staphylococcus aureus TCH1516 were evaluated.

Total synthesis of (±)-Marinopyrrole a and its library as potential antibiotic and anticancer agents

The first total synthesis of marine natural product, (±)- marinopyrrole A, has been accomplished via a nine-step synthesis in an overall yield of 30%. A small focused library based on marinopyrrole has been designed and synthesized. The scope of chemistry was investigated, and a robust chemistry suitable for library synthesis has been developed in the current study. The method that we have developed has made it possible to generate diverse analogues based on structurally novel marinopyrroles for study of potential antibiotic and anticancer activities.

Total synthesis of (±)-marinopyrrole a via copper-mediated N-arylation

The total synthesis of the racemic form of the marine alkaloid marinopyrrole A is described. The characteristic 1,3′-bipyrrole core was constructed by a copper-mediated N-arylation process under microwave irradiation.

Structures, reactivities, and antibiotic properties of the marinopyrroles A-F

Cultivation of actinomycete strain CNQ-418, retrieved from a deep ocean sediment sample off the coast of La Jolla, CA, has provided marinopyrroles A-F. Sharing just 98% 16S rRNA gene sequence identity with S. sannurensis, the strain likely represents a new Streptomyces species. The metabolites contain an unusual 1,3′-bipyrrole core decorated with several chlorine and bromine substituents and possess marked antibacterial activity against methicillin-resistant Staphylococcus aureus (MRSA). The congested N,C-biaryl bond establishes an axis of chirality that, for marinopyrroles A-E, is configurationally stable at room temperature. Moreover, the natural products are fashioned strictly in the M-configuration. The Paal-Knorr condensation was adapted for the synthesis of the 1,3′-bipyrrole core. Halogenation of this material with N-bromosuccinimide cleanly furnished the 4,4′,5,5′- tetrahalogenated core that characterizes this class of marine-derived metabolites.