- Expedient total syntheses of preclathridine A and clathridine A
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A short and operationally simple total synthesis of two Leucetta-derived marine alkaloids has been developed, which rely on position specific halogen-metal exchange to introduce the benzyl-substituted side chain. Introduction of the C2 amine group by lith
- Koswatta, Panduka B.,Lovely, Carl J.
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- V-shaped fluorophores with a 1-methyl-4,5-bis(arylethynyl)imidazole skeleton displaying solid-state fluorescence, acid responsiveness, and remarkable fluorescence solvatochromism
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Novel V-shaped fluorophores with an imidazole skeleton composed of arylethynyl moieties were developed. Their HOMO-LUMO energy gaps were well controlled by the introduction of electron-withdrawing or -donating groups in the aryl moiety. Compounds with different substituents at the 4- and 5-positions were selectively synthesized exploiting the difference in reactivity between the iodo and bromo groups. All compounds synthesized displayed fluorescence not only in solution but also in the solid state. The compound with a donor-acceptor structure displayed a fluorescence maximum with a wavelength over 500 nm and a large Stokes shift of about 150 nm, due to its intramolecular charge transfer character. In the solid state, the synthesized compounds have planar structures, indicating an expansion of π-conjugation. Upon exposure of the compounds in the solid state to acid vapor, the fluorescence of the compounds with acceptor groups was quenched, and that of the others shifted to longer wavelengths.
- Miura, Youhei,Kobayashi, Kotaro,Yoshioka, Naoki
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- MYST FAMILY HISTONE ACETYLTRANSFERASE INHIBITORS
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The present disclosure provides compounds, pharmaceutically acceptable compositions thereof, and methods of using the same.
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Paragraph 0293-0295; 0292
(2019/06/19)
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- PURINONES AS UBIQUITIN-SPECIFIC PROTEASE 1 INHIBITORS
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The application relates to inhibitors of USP1 useful in the treatment of cancers, and other USP1 associated diseases and disorders, having the Formula: (I), where R1, R2, R3, R3', R4, R5, X1, X2, X3, X4, and n are described herein.
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Paragraph 00394
(2017/06/12)
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- Total synthesis and cytotoxicity of Leucetta alkaloids
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The total synthesis of a number of representative natural products isolated from Leucetta and Clathrina sponges containing a polysubstituted 2-aminoimidazole are described. These syntheses take advantage of the site specific metallation reactions of 4,5-diiodoimidazoles resulting in the syntheses of three different classes of Leucetta derived natural products. The cytotoxicities of these natural products, along with several precursors in MCF7 cells were determined through an MTT growth assay. For comparative purposes a series of naphthimidazole-containing family members are included.
- Koswatta, Panduka B.,Kasiri, Sabha,Das, Jayanta K.,Bhan, Arunoday,Lima, Heather M.,Garcia-Barboza, Beatriz,Khatibi, Nicole N.,Yousufuddin, Muhammed,Mandal, Subhrangsu S.,Lovely, Carl J.
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p. 1608 - 1621
(2017/02/26)
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- Ruthenium piano-stool complexes bearing imidazole-based PN ligands
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A variety of piano-stool complexes of cyclopentadienyl ruthenium(II) with imidazole-based PN ligands have been synthesized starting from the precursor complexes [CpRu(C10H8)]PF6, [CpRu(NCMe) 3]PF6 and [CpRu(PPh3)2Cl]. PN ligands used are imidazol-2-yl, -4-yl and -5-yl phosphines. Depending on the ligand and precursor different types of coordination modes were observed; in the case of polyimidazolyl PN ligands these were κ1P-monodentate, κ2P,N-, κ2N,N- and κ3N,N,N- chelating and μ-κP:κ2N,N-brigding. The solid-state structures of [CpRu(1a)2Cl ]·H2O (5 .H2O) and [{CpRu(μ-κ2-N,N- κ'1-P-2b)}2](C6H5PO 3H)2(C6H5PO3H 2)2, a hydrolysis product of the as well determined [{CpRu(2b)}2](PF6)2.2CH 3CN (7b.2CH3CN) were determined (1a = imidazol-2-yldiphenyl phosphine, 2b = bis(1-methylimidazol-2-yl)phenyl phosphine, 3a = tris(imidazol-2-yl)phosphine). Furthermore, the complexes [CpRu(L)2]PF6 (L = imidazol-2-yl or imidazol-4-yl phosphine) have been screened for their catalytic activity in the hydration of 1-octyne.
- Kunz, Peter C.,Thiel, Indre,Noffke, Anna Louisa,Rei?, Guido J.,Mohr, Fabian,Spingler, Bernhard
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supporting information; experimental part
p. 33 - 40
(2012/01/06)
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- Preparation and diels-alder chemistry of 4-vinylimidazoles
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(Chemical Equation Presented) Various 4-vinylimidazole derivatives have been prepared from the corresponding 4-iodoimidazoles or from urocanic acid. Several methods for the elaboration of these vinylimidazoles and their Diels-Alder reactions are reported. All of the vinylimidazoles prepared in the course of this study react with N-phenylmaleimide quite readily with mild thermal activation providing a single cycloadduct, in most cases the initial, nonaromatic adduct. With more electron rich substrates, there is a tendency for these initial cycloadducts to undergo aromatization, ene reaction, and oxidation although this can be circumvented to a large extent by the choice of reaction conditions. Limited reactions were observed with other dienophiles, providing the expected cycloadducts in most cases, although an abnormal adduct was obtained in one case with dimethyl acetylene dicarboxylate. These substrates also participate in regioselective Diels-Alder reactions with monoactivated dienophiles, but require fairly forcing conditions, thus only providing the aromatized cycloadducts in modest yields. An investigation of substituent effects at the 2-position of the imidazole moiety was undertaken, in which electron-donating and weakly electron-withdrawing substituents are tolerated. In addition, several substrates with terminally substituted vinyl moieties have been investigated.
- Lovely, Carl J.,Du, Hongwang,Sivappa, Rasapalli,Bhandari, Manojkumar R.,He, Yong,Dias, H. V. Rasika
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p. 3741 - 3749
(2008/02/04)
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- A convenient synthesis of 1,4-disubstituted imidazoles
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An efficient method for the regioselective protection of 4-alkyl-, 4-iodo, 4-vinylimidazoles has been developed via an alkylation-isomerization sequence with various imidazole-protecting groups. The initially formed mixture of 4/5-alkyl-, 4/5-iodo, and 4/5-vinylimidazoles are isomerized to the corresponding 4-isomers on treatment of a DMF solution with a small amount of RX and heating at 75°C.
- He, Yong,Chen, Yingzhong,Du, Hongwang,Schmid, Lesley A.,Lovely, Carl J.
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p. 5529 - 5532
(2007/10/03)
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- Regioselective synthesis of 1-benzyl- and 1-methyl-4- vinylimidazole and their reactions with N-phenylmaleimide
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The regioselective synthesis of 1-benzyl- and 1-methyl-4- vinylimidazole from 4,5-diiodoimidazole is described. Their Diels-Alder reactions with N-phenylmaleimide provide a variety of adducts, including the anticipated enamine and the corresponding aromatized isomer. However, additional products including ene adducts, a bis Diels-Alder adduct and oxidation products were isolated.
- Lovely, Carl J.,Du, Hongwang,Rasika Dias
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- First total synthesis of fungerin an antifungal alkaloid from fusarium sp.
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The first total synthesis of fungerin 1, a new antifungal alkaloid, is described. Starting from a 4,5-diiodoimidazole derivative, the procedure involves regioselective prenylation and Heck type reaction steps to give 1 in high yield.
- Benhida, Rachid,Lezama, Ruth,Fourrey, Jean-Louis
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p. 5963 - 5964
(2007/10/03)
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- Metal-Halogen Exchange Reactions of Mono- and Poly-halogenoimidazoles
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4(5)-Bromoimidazole gave a mixture of 4- and 5-bromo-1-methylimidazole on treatment with 1 or 2 mol equiv. of n-butyl-lithium in ether or THF under various reaction conditions followed by addition of dimethyl sulphate. 5-Iodo and 2,4,5-tribromo-1-methylim
- Iddon, Brian,Lim, Bee Lan
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p. 735 - 739
(2007/10/02)
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