Racemic marinopyrrole B by total synthesis

Cheng, Ping; Clive, Derrick L. J.; Fernandopulle, Shimal C.; Chen, Zhenhua

doi:10.1039/c2cc37110c

Cited by 25 publications

(30 citation statements)

References 25 publications

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“…64,65,69,70 The first, and thus far only, synthesis of marinopyrrole B (29) was reported in 2013 by Cheng et al (not shown), whereby the bipyrrole core in this case was instead generated through alkylation of a trihalogenated pyrrole, which underwent further manipulations to complete a Paal-Knorr construction of the second pyrrole ring, a precursor which allowed for the generation of rac-29. 71 Scheme 5: Convergent total synthesis of racemic marinopyrrole A (28).…”

Section: Marinopyrroles: Determination Of Enzymatically-imposed Atropmentioning

confidence: 99%

A twist of nature – the significance of atropisomers in biological systems

2015

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. (2015). A twist of nature-the significance of atropisomers in biological systems. Natural Product Reports: a journal of current development in bioorganic chemistry, 32 (11), 1562-1583. A twist of nature-the significance of atropisomers in biological systems AbstractRecently identified natural atropisomeric compounds with potential medicinal applications are presented. The ability of natural receptors to possess differential binding between atropisomers is an important factor when considering active and inactive atropisomeric drugs, and has required the development of new techniques for atropselective synthesis of desired targets. Advances in this field therefore have significant relevance to modern pharmaceutical and medicinal chemistry. The atropisomeric natural products discussed include hibarimicinone, flavomannins, talaromannins, viriditoxin, rugulotrosin A, abyssomicin C, marinopyrroles, dixiamycins, streptorubin B, ustiloxins A-F, haouamine A, bisnicalaterines, and tedarene B, all of which show significant potential as leads in antibiotic, antiviral and anticancer studies. The importance for the development of common practices regarding atropisomer recognition and classification is also emphasized. AbstractRecently identified natural atropisomeric compounds with potential medicinal applications are presented. The ability of natural receptors to possess differential binding between atropisomers is an important factor when considering active and inactive atropisomeric drugs, and has required the development of new techniques for atropselective synthesis of desired targets. Advances in this field therefore have significant relevance to modern pharmaceutical and medicinal chemistry. The atropisomeric natural products discussed include hibarimicinone, flavomannins, talaromannins, viriditoxin, rugulotrosin A, abyssomicin C, marinopyrroles, dixiamycins, streptorubin B, ustiloxins A-F, haouamine A, bisnicalaterines, and tedarene B, all of which show significant potential as leads in antibiotic, antiviral and anticancer studies. The importance for the development of common practices regarding atropisomer recognition and classification is also emphasized.

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Section: Marinopyrroles: Determination Of Enzymatically-imposed Atropmentioning

confidence: 99%

A twist of nature – the significance of atropisomers in biological systems

2015

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“…Biosynthesis of marinopyrrole A via an N , C -bipyrrole homocoupling catalyzed by two flavin-dependent halogenases was reported by the Moore group [2], and racemic marinopyrrole B by total synthesis and a review of the marinopyrroles were reported by the Clive group [3,4]. After optimization of the key step to avoid the formation of an oxazepine byproduct [5] that was reported in our first total synthesis of marinopyrroles [8], we published the most potent symmetrical marinopyrrole derivative against MRSA and methicillin-resistant Staphylococcus epidermidis (MRSE) [6].…”

Section: Introductionmentioning

confidence: 99%

Marinopyrrole Derivatives as Potential Antibiotic Agents against Methicillin-Resistant Staphylococcus aureus (III)

et al. 2014

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The marine natural product, marinopyrrole A (1), was previously shown to have significant antibiotic activity against Gram-positive pathogens, including methicillin-resistant Staphylococcus aureus (MRSA). Although compound (1) exhibits a significant reduction in MRSA activity in the presence of human serum, we have identified key modifications that partially restore activity. We previously reported our discovery of a chloro-derivative of marinopyrrole A (1a) featuring a 2–4 fold improved minimum inhibitory concentration (MIC) against MRSA, significantly less susceptibility to serum inhibition and rapid and concentration-dependent killing of MRSA. Here, we report a novel fluoro-derivative of marinopyrrole A (1e) showing an improved profile of potency, less susceptibility to serum inhibition, as well as rapid and concentration-dependent killing of MRSA.

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“…Due to their novel class of molecular structures and promising biological properties, marinopyrroles have attracted considerable attention [11,12,13,14,15,16,17,18,19]. We reported the first total synthesis of (±)-marinopyrrole A, along with 12 derivatives in early 2010 [12].…”

Section: Introductionmentioning

confidence: 99%

“…Recently, the Moore group published biosynthesis of marinopyrrole A via an N , C -bipyrrole homocoupling catalyzed by two flavin-dependent halogenases [17]. Most recently, racemic marinopyrrole B was reported by total synthesis from the Clive group [18]. During the preparation of this manuscript, a review of the marinopyrroles appeared [19].…”

Section: Introductionmentioning

confidence: 99%

Marinopyrrole Derivatives as Potential Antibiotic Agents against Methicillin-Resistant Staphylococcus aureus (II)

et al. 2013

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Methicillin-resistant Staphylococcus aureus (MRSA) continues to be a major problem, causing severe and intractable infections worldwide. MRSA is resistant to all beta-lactam antibiotics, and alternative treatments are limited. A very limited number of new antibiotics have been discovered over the last half-century, novel agents for the treatment of MRSA infections are urgently needed. Marinopyrrole A was reported to show antibiotic activity against MRSA in 2008. After we reported the first total synthesis of (±)-marinopyrrole A, we designed and synthesized a series of marinopyrrole derivatives. Our structure activity relationship (SAR) studies of these novel derivatives against a panel of Gram-positive pathogens in antibacterial assays have revealed that a para-trifluoromethyl analog (33) of marinopyrrole A is ≥63-, 8-, and 4-fold more potent than vancomycin against methicillin-resistant Staphylococcus epidermidis (MRSE), methicillin-susceptible Staphylococcus aureus (MSSA) and MRSA, respectively. The results provide valuable information in the search for new-generation antibiotics.

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Racemic marinopyrrole B by total synthesis

Cited by 25 publications

References 25 publications

A twist of nature – the significance of atropisomers in biological systems

A twist of nature – the significance of atropisomers in biological systems

Marinopyrrole Derivatives as Potential Antibiotic Agents against Methicillin-Resistant Staphylococcus aureus (III)

Marinopyrrole Derivatives as Potential Antibiotic Agents against Methicillin-Resistant Staphylococcus aureus (II)

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