42041-50-9Relevant academic research and scientific papers
Facile dearomatizing radical arylation of furan and thiophene
Crich, David,Patel, Mitesh
, p. 3625 - 3628 (2005)
(Chemical Equation Presented) In the presence of catalytic diphenyl diselenide, reduced in situ to benzeneselenol, tributyltin hydride and V-70 promote the addition of aryl iodides to furan and thiophene. The adduct radicals are trapped by the selenol to give the 2-aryl-2,3-dihydro and 2-aryl-2,5-dihydro heterocyclic products. When the iodide is an o-iodophenol, a cyclization follows the radical addition and provides bridged bicyclic acetals.
Novel Thermal Rearrangement of Tetrahydro-azirinocyclobutabenzofuran Derivatives
Kurita, Jyoji,Sakai, Hiroichi,Yamada, Sachiko,Tsuchiya, Takashi
, p. 285 - 286 (1987)
Thermolysis of the 1a,1b,6b,6c-tetrahydro-azirinocyclobutabenzofurans (3) results in ring transformations to form the benzofuropyrroles (5) and their -isomers (6).
C–H Arylation of N-Heteroarenes under Metal-Free Conditions and its Application towards the Synthesis of Pentabromo- and Pentachloropseudilins
Kumar, Mukesh,Sharma, Shweta,Sil, Parijat,Kushwaha, Manoj,Mayor, Satyajit,Vishwakarma, Ram A.,Singh, Parvinder Pal
, p. 3591 - 3598 (2019/06/20)
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.
Two-step total synthesis of an anti-MRSA and myosin-inhibiting marine natural product pentabromopseudilin via Suzuki-Miyaura coupling of a MIDA boronate ester
Kum, Dong-Young,Nazari, Mohamad,McPhail, Kerry L.,Cooper, Christina S.,Suyama, Takashi L.
, p. 3374 - 3376 (2017/08/03)
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
Circularly Polarized Luminescence from Helically Chiral N,N,O,O-Boron-Chelated Dipyrromethenes
Alnoman, Rua B.,Rihn, Sandra,O'Connor, Daniel C.,Black, Fiona A.,Costello, Bernard,Waddell, Paul G.,Clegg, William,Peacock, Robert D.,Herrebout, Wouter,Knight, Julian G.,Hall, Michael J.
, p. 93 - 96 (2016/01/25)
Helically chiral N,N,O,O-boron chelated dipyrromethenes showed solution-phase circularly polarized luminescence (CPL) in the red region of the visible spectrum (λem(max) from 621 to 663 nm). The parent dipyrromethene is desymmetrised through O
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
Martin, Rene,Risacher, Celia,Barthel, Andre,Jaeger, Anne,Schmidt, Arndt W.,Richter, Sabine,Boehl, Markus,Preller, Matthias,Chinthalapudi, Krishna,Manstein, Dietmar J.,Gutzeit, Herwig O.,Knoelker, Hans-Joachim
, p. 4487 - 4505 (2014/08/05)
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
Schwalm, Cristiane S.,De Castro, Ilton B.D.,Ferrari, Jailton,De Oliveira, Fábio L.,Aparicio, Ricardo,Correia, Carlos Roque D.
, p. 1660 - 1663 (2012/04/10)
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
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Page/Page column 16-17, (2011/05/08)
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
Reactions of 2-(pyrrol-1-yl)benzyl radicals and related species under flash vacuum pyrolysis conditions
Cadogan,Clark, Bernard A. J.,Ford, Daniel,MacDonald, Ranald J.,MacPherson, Andrew D.,McNab, Hamish,Nicolson, Iain S.,Reed, David,Sommerville, Craig C.
experimental part, p. 5173 - 5183 (2010/04/03)
2-(Pyrrol-1-yl)phenoxyl, aminyl, thiophenoxyl and benzyl radicals 2a-2d, respectively, were generated in the gas-phase under flash vacuum pyrolysis conditions. In all cases except the phenoxyl, cyclisation took place providing acceptable synthetic routes to the fused heterocycles 11, 14 and 15, respectively. Only sigmatropic rearrangement products were isolated, in low yields, from the phenoxyl 2a. The pyrrolo[1,2-a]benzimidazole 11 adopts the 1H-tautomer exclusively in chloroform solution. Electrophilic substitution reactions of pyrrolo[2,1-b]benzothiophene 14 were studied, including protonation, deuterium exchange, Vilsmeier formylation and reaction with dimethyl acetylenedicarboxylate. 2-(2,5-Diarylpyrrol-1-yl)thiophenoxyl, phenoxyl and aminyl radicals 23a-f, were also generated in the gas-phase under similar conditions. The thiophenoxyls 23a/b gave extremely complex pyrolysate mixtures in which primary cyclisation products were formed by attack of the radical at the pyrrrole ring and attack at the ipso-, ortho- and meta- positions of the aryl ring. Secondary pyrolysis products were obtained by specific sigmatropic shifts of the N-aryl group. The 2,5-di(thien-2-yl)thiophenoxyl radical 23c gave the pyrrolobenzothiazole 31c as the only cyclisation product in low yield. FVP of the phenoxyl and aminyl radical generators 26d and 26f, respectively, gave 3-arylpyrrolo[1,2-f]phenanthridines 46d and 46f, respectively, by a hydrogen transfer-cyclisation mechanism.
Total synthesis of pentabromo- and pentachloropseudilin, and synthetic analogues-allosteric inhibitors of myosin ATPase
Martin, Rene,Jaeger, Anne,Bohl, Markus,Richter, Sabine,Fedorov, Roman,Manstein, Dietmar J.,Gutzeit, Herwig O.,Knolker, Hans-Joachim
scheme or table, p. 8042 - 8046 (2010/01/16)
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
