- Fungal Dioxygenase AsqJ Is Promiscuous and Bimodal: Substrate-Directed Formation of Quinolones versus Quinazolinones
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Previous studies showed that the FeII/α-ketoglutarate dependent dioxygenase AsqJ induces a skeletal rearrangement in viridicatin biosynthesis in Aspergillus nidulans, generating a quinolone scaffold from benzo[1,4]diazepine-2,5-dione substrates. We report that AsqJ catalyzes an additional, entirely different reaction, simply by a change in substituent in the benzodiazepinedione substrate. This new mechanism is established by substrate screening, application of functional probes, and computational analysis. AsqJ excises H2CO from the heterocyclic ring structure of suitable benzo[1,4]diazepine-2,5-dione substrates to generate quinazolinones. This novel AsqJ catalysis pathway is governed by a single substituent within the complex substrate. This unique substrate-directed reactivity of AsqJ enables the targeted biocatalytic generation of either quinolones or quinazolinones, two alkaloid frameworks of exceptional biomedical relevance.
- Einsiedler, Manuel,Jamieson, Cooper S.,Maskeri, Mark A.,Houk, Kendall N.,Gulder, Tobias A. M.
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supporting information
p. 8297 - 8302
(2021/03/01)
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- Facile synthesis of 1,4-benzodiazepine-2,5-diones and quinazolinones from amino acids as anti-tubercular agents
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A family of 1,4-benzodiazepine-2,5-diones and quinazolinones with diverse substituents at the C-3 position were synthesized via a novel, simple and convenient methodology using H2PtCl6 as the catalyst. The substitution at the C-3 pos
- Anil, Seegehalli M.,Shobith, Rangappa,Kiran, Kuppalli. R.,Swaroop, Toreshettahally R.,Mallesha, Ningegowda,Sadashiva, Maralinganadoddi P.
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p. 182 - 187
(2019/01/04)
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- BENZODIAZEPINE AND BENZOPIPERAZINE ANALOG INHIBITORS OF HISTONE DEACETYLASE
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This invention relates to compounds for the inhibition of histone deacetylase More particularly, the invention provides for compounds of formula (I): wherein A, B, D, E, X1, X2, X3, X4 and n are as defined in the specification A method of inhibiting histone deacetylase in a cell, the method comprising contacting the cell with a compound of formula (I), in an amount sufficient to inhibit histone deacetylase, is also disclosed.
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Page/Page column 81; 85
(2010/11/26)
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- One pot conversion of azido arenes to N-arylacetamides and N-arylformamides: Synthesis of 1,4-benzodiazepine-2,5-diones and fused [2,1-b]quinazolinones
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Sodium iodide in acidic media has been employed for the synthesis of N-arylformamides and N-arylacetamides. The NaI/acetic acid reagent system has also been extended for the synthesis of 1,4-benzodiazepine-2,5-diones, pyrrolo[2,1-c][1,4]benzodiazepine-5,11-diones, and fused [2,1-b]quinazolinones.
- Kamal, Ahmed,Ramana, A. Venkata,Reddy, K. Srinivasa,Ramana, K. Venkata,Hari Babu,Prasad, B. Rajendra
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p. 8187 - 8190
(2007/10/03)
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- New routes to 1,4-benzodiazepin-2,5-diones
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1,4-benzodiazepin-2,5-diones have been synthesized in good overall yields by two routes, the first one by cyclisation of dipeptides prepared from Boc anthranilic acid and α-amino acid methyl esters, the second one by reaction of N-carboxy α-amino acid anhydrides with Boc anthranilic acid.
- Akssira,Boumzebra,Kasmi,Dahdouh,Roumestant,Viallefont
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p. 9051 - 9060
(2007/10/02)
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