Lewis Acid-Catalyzed One-Pot, Three-Component Route to Chiral 3,3‘-Bipyrroles

Dey, Sumit; Pal, Churala; Nandi, Debkumar; Giri, Venkatachalam S.; Zaidlewicz, M.; Krzemiński, M.; Smentek, Lidia; Hess, B. Andes; Gawroński, Jacek; Kwit, Marcin; Babu, N. Jagadeesh; Nangia, and Ashwini; Jaisankar, Parasuraman

doi:10.1021/ol800115p

Cited by 39 publications

(16 citation statements)

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“…They are key intermediates for the synthesis of a variety of biologically active molecules [4-7] and act as functional materials [8]. Compounds that bearing a pyrrole ring [9] show several biological and pharmacological activities s uc h as antit umor [10 ], anti bacter i al [11 ], and its derivatives have been reported, as well as the Paal-Knorr condensation reaction [24,25], catalytic dehydrogenation reactions [26], coupling reactions [26][27][28], and a double Michael addition reaction [29], and the metal-catalyzed 1, 3-dipolar cycloaddition of azomethine ylides [30]. However, the literature covers limited inform ation for the synthesis bipyrroles, suggesting that methods to their synthesis are limiting.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of novel 2, 3'-bipyrrole derivatives from chalcone and amino acids as antitumor agents.

et al. 2020

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A series of a novel 2, 3'-bipyrrole derivatives was synthesized via the reaction of chalcone, (E)-1-(furan-2-yl)-3-(1H-pyrrol-2yl) prop-2-en-one, with different amino acids in an alkaline medium. The reaction proceeds throughout the condensation of the amino acids with chalcone to give imine intermediate consequent by decarboxylation, and then intramolecular cyclization to yield 2, 3'-bipyrrole derivatives. Antitumor activities of the newly synthesized bipyrrole were evaluated against different six cancer cell lines, and compounds (3d, 3e, 3c and 3h) derivatives showed the strongest anticancer activity amongst the studied compounds. Compound (3h) showed the broadest spectrum of anticancer activity against all cell lines tested. The results of this work offer a basis for further study of selected 2, 3'-bipyrrole derivatives as antitumor agents. drowyeKs: amino acids, pyrrole, bipyrrole, furan, antitumor, chalcone. antioxidative [12], anti-inflammatory [13], and antifungal properties [14]. Bipyrroles are an appreciated pioneer for the synthesis of several marine natural products [15]. Marinopyrroles A (1) and B (2) (Figure 1) with a unique 1,3'-bipyrrole structure display anti-bacterial results towards methicillin-resistant Staphylococcus aureus (MRSA) and cytotoxicity contrary to specific human cancer cells [16-18]. Also, bipyrroles and their derivatives are the basic components in several natural products and medicines (e.g., prodigiosin) [19-23]. Due to the promising of bipyrroles, they have of the interest of several researchers. Some approaches to the bipyrrole

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Section: Introductionmentioning

confidence: 99%

Synthesis of novel 2, 3'-bipyrrole derivatives from chalcone and amino acids as antitumor agents.

et al. 2020

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“…Even these simple considerations suggest that the stability of 3,3′‐linked derivatives is less than that of the corresponding 2,2′‐linked counterparts; this is consistent with the fact that few methods for their preparation have been developed. 3,3′‐Linked bispyrroles have been generated by Gleiter via Pd‐catalyzed rearrangements of bisazacyclodiynes, Barton–Zard syntheses of pyrrole derivatives, the transformation of 1,4‐diketone dioximes with acetylene, oxidative couplings and by Michael addition reactions involving diaroyl acetylene, 1,3‐dicarbonyls with ammonium acetate and copper‐catalyzed starting from homopropargylic amines . Magnus and co‐workers were able to prepare N ‐tosyl‐substituted oligopyrroles such as 3 via a repetitive sequence using cyanosubstituted alkenes (e.g.…”

Section: Introductionmentioning

confidence: 99%

Reactions of 3,3′‐Linked Bispyrroles with Carbon Electrophiles

2019

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The reactivity of 3,3′‐linked bispyrroles, easily accessible by ring‐enlargement reactions of donor–acceptor cyclopropanes, towards various carbon electrophiles was investigated. A biscyclopropanated furan, equipped with imines as acceptor units, was converted by rearrangement and subsequent elimination of water to 3,3′‐linked bispyrroles. Thereby the nucleophilic 2‐position of the pyrroles stayed unsubstituted, thus permitting a further reaction with electrophiles. The heterocycles were treated with oxalyl chloride to form a new six‐membered ring between the pyrrolic subunits. The 1,2‐diketone moiety in these species was used as a starting point to extend the π‐system via a condensation reaction with aromatic 1,2‐diamines. The reaction of 3,3′‐linked bispyrroles with the phosgene surrogate triphosgene led to a seven‐membered anhydride. The use of the Vilsmeier reagent led to a formylation of the bispyrroles. Furthermore, a direct oxidative coupling between two bispyrroles resulted in a previously unknown linkage (3,3′:2′,2′′:3′′,3′′′) between four pyrrole subunits.

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“…[8] In contrast, the number of reports concerning the 3,3'-linkage of pyrrole moieties is much lower. [9,10] 3,3'-Linked dimers have been accessed, for instance, by Pd-catalyzed rearrangements of N-bridged diynes, [11] by Barton-Zard synthesis on pyrrole derivatives, [12] or by oxidative couplings. [13] Potential crosscoupling reactions suffer from the heavy accessibility of 3-substituted pyrroles.…”

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confidence: 99%