10245-81-5

Usage

Uses

Used in Pharmaceutical Industry:
Pentabromopseudilin is used as an antibiotic agent for its antibiotic action against various types of bacteria. The compound has demonstrated the ability to inhibit bacterial growth, making it a potential candidate for the development of new antibiotics to combat bacterial infections.
Used in Research and Development:
Pentabromopseudilin is also used as a research tool to study the mechanisms of autoinhibition in Chromobacterium and other similar bacteria. Understanding these mechanisms can provide insights into bacterial behavior and contribute to the development of targeted therapies and treatments for bacterial infections.

InChI:InChI=1/C10H4Br5NO/c11-3-1-4(9(17)5(12)2-3)8-6(13)7(14)10(15)16-8/h1-2,16-17H

Upstream product

• 10245-83-7 3,4,5-Tribrom-2-(3',5'-dibrom-2'-methoxyphenyl)-1H-pyrrol 
• 74303-03-0 2-(2-benzyloxyphenyl)-1H-pyrrole 
• 856438-49-8 allyl-[1-(2-benzyloxy-phenyl)-prop-2-ynyl]-carbamic acid methyl ester 
• 61657-65-6 3,5-dibromo-2-methoxybenzaldehyde 
• 42041-50-9 2-(2-hydroxyphenyl)-1H-pyrrole 
• 90-04-0 2-methoxy-phenylamine 
• 250591-69-6 tert-butyl 2-(2-methoxyphenyl)-1H-pyrrole-1-carboxylate 
• 100200-70-2 N-(2-methoxybenzylidene)-p-toluenesulfonamide 
• 135-02-4 ortho-anisaldehyde 
• 1198777-65-9 2-(2-methoxyphenyl)-1-(p-tolylsulfonyl)-2,3-dihydro-1H-pyrrole 
• 1198777-62-6 N-[1-(2-methoxyphenyl)-but-3-ynyl]-4-methylbenzenesulfonamide 
• 1198777-58-0 N-[1-(2-methoxyphenyl)-4-(trimethylsilyl)but-3-ynyl]-4-methylbenzenesulfonamide 
• 492-95-5 2-methoxyphenyldiazonium tetrafluoroborate 
• 1364322-48-4 C₁₉H₁₇NO₃ 

Downstream Products

• 882-33-7 diphenyldisulfane 
• 10245-83-7 3,4,5-Tribrom-2-(3',5'-dibrom-2'-methoxyphenyl)-1H-pyrrol 

Relevant academic research and scientific papers

Two-step total synthesis of an anti-MRSA and myosin-inhibiting marine natural product pentabromopseudilin via Suzuki-Miyaura coupling of a MIDA boronate ester

A marine natural product isolated from Pseudoalteromonas sp., pentabromopseudilin, with promising anti-MRSA and myosin ATPase inhibition activities was synthesized in two steps using recently developed MIDA boronate Suzuki-Miyaura coupling technology. Add

C–H Arylation of N-Heteroarenes under Metal-Free Conditions and its Application towards the Synthesis of Pentabromo- and Pentachloropseudilins

Herein, we are reporting metal-free conditions for radical initiation and direct C–H arylation of N-heteroarenes. Starting from aniline, the corresponding arenediazonium salt generated in situ is reduced to an aryl radical in the presence of chloropromazine hydrochloride, a new reagent for this application. The optimized procedures are mild, operationally simple, and are working successfully with more diverse substrates in comparison to reported methods. The optimized method is also employed for the synthesis of marine natural products Pentabromo- and Pentachloropseudilins (PBP/PCP). In the present study, we also validated the potential of the Pentachloropseudilin (PCP), thus synthesized, for inhibition of Myosin1 function in mammalian cells and confirmed that PCP phenocopies Myosin1c depletion in cells.

Silver(I)-catalyzed route to pyrroles: Synthesis of halogenated pseudilins as allosteric inhibitors for myosin atpase and x-ray crystal structures of the protein-inhibitor complexes

The pentahalogenated 2-arylpyrrole-type alkaloids pentabromopseudilin and pentachloropseudilin represent a new class of isoform-specific allosteric inhibitors of myosin ATPase. Herein, we describe an application of the silver(I)-catalyzed cycloisomerizati

Synthesis of pentabromopseudilin and other arylpyrrole derivatives via Heck arylations

Pentrabromopseudilin and other 2 and 3-arylpyrrole derivatives were synthesized through the Heck-Matsuda reaction involving endocyclic enecarbamates and N-protected 3-pyrrolines, respectively. The overall processes permitted an easy and efficient access t

MEANS FOR TREATING MYOSIN-RELATED DISEASES

The present invention provides a method of designing a modulator of a myosin, the method comprising molecular modeling of a compound such that the modeled compound interacts with at least three amino acid residues of said myosin, said residues being selec

Total synthesis of pentabromo- and pentachloropseudilin, and synthetic analogues-allosteric inhibitors of myosin ATPase

Stopping myo: The total syntheses of the title compounds have been achieved using a highly efficient silver(I)- catalyzed cyclization of N-tosyl-homopropargylamines. The pseudilin derivatives represent a novel class of myosin inhibitors. A new allosteric

A re(V)-catalyzed C-N bond-forming route to human lipoxygenase inhibitors

(Chemical Equation Presented) A regioselective synthesis of propargylamines by the coupling of propargyl alcohols with tosylamines and carbamates catalyzed by an air-and moisture-tolerant rhenium-oxo complex is described. The ability to couple functionali

A Novel [3+2] Cycloaddition Approach to Nitrogen Heterocycles via Phosphine-Catalyzed Reactions of 2,3-Butadienoates or 2-Butynoates and Dimethyl Acetylenedicarboxylate with Imines: A Convenient Synthesis of Pentabromopseudilin

The reactivity of a new three carbon synthon, generated in situ from the reaction of 2,3-butadienoates 2-butynoates with an appropriate phosphine as the catalyst, toward the electron-deficient imines is described. Triphenylphosphine-catalyzed reaction of methyl 2,3-butadienoate with N-sulfonylimines gave the single [3+2] cycloadduct in excellent yield; tributylphosphine-catalyzed reaction of methyl 2,3-butadienoate or 2-butynoate with N-tosylimines afforded the corresponding [3+2] cycloadduct as the major product along with a small amount of the three components adduct. Aliphatic N-tosylimines gave moderate yield for this reaction. In addition, a new phosphine-catalyzed cyclization reaction of dimethyl acetylenedicarboxylate with N-tosylimines is also described. A reaction mechanism is proposed. Further elaborations of the cycloaddition products and the synthesis of pentabromopseudilin using this method are exemplified.

Marine Bacteria, I. - Synthesis of Pentabromopseudiline, a Cytotoxic Phenylpyrrole from Alteromonas luteo-violaceus

A new synthesis of 2,3,4-tribromo-5-(3,5-dibromo-2-hydroxyphenyl)pyrrole (1a, pentabromopseudiline), an antibiotic, enzymeinhibitory and cytotoxic active constituent of the marine bacterium Alteromonas luteo-violaceus, is described.For investigation of structure-activity relationships further 2-phenylpyrroles are investigated.Key step in their synthesis is the Grignard reaction of 2-(1,3-dioxan-2-yl)ethylmagnesium bromide (9d) with benzoyl chlorides yielding γ-phenyl-γ-ketoaldehydes 24, and the Paal-Knorr cyclisation of the latter. - Key Words: Alteromonas luteo-violaceus / Bromopyrrole / Marine bacteria / Pentabromopseudiline