112811-64-0Relevant articles and documents
Identification of an ethyl 5,6-dihydropyrazolo[1,5-c]quinazoline-1-carboxylate as a catalytic inhibitor of DNA gyrase
Aguirre, Arturo L.,Chheda, Pratik R.,Groves, Natalie P.,Held, Hailey A.,Hiasa, Hiroshi,Kerns, Robert J.,Lentz, Sarah R. C.
, (2020)
Fluoroquinolones are a class of antibacterial agents used clinically to treat a wide array of bacterial infections and target bacterial type-II topoisomerases (DNA gyrase and topoisomerase IV). Fluoroquinolones, however potent, are susceptible to bacterial resistance with prolonged use, which limits their use in the clinic. Quinazoline-2,4-diones also target bacterial type-II topoisomerases and are not susceptible to bacterial resistance similar to fluoroquinolones, however, their potency pales in comparison to fluoroquinolones. To meet the increasing demand for antibacterial development, nine modified quinazoline-2,4-diones were developed to probe quinazoline-2,4-dione structure modification for possible new binding contacts with the bacterial type-II topoisomerase, DNA gyrase. Evaluation of compounds for inhibition of the supercoiling activity of DNA gyrase revealed a novel ethyl 5,6-dihydropyrazolo[1,5-c]quinazoline-1-carboxylate derivative as a modest inhibitor of DNA gyrase, having an IC50 of 3.5 μM. However, this ethyl 5,6-dihydropyrazolo[1,5-c]quinazoline-1-carboxylate does not trap the catalytic intermediate like fluoroquinolones or typical quinazoline-2,4-diones do. Thus, the ethyl 5,6-dihydropyrazolo[1,5-c]quinazoline-1-carboxylate derivative discovered in this work acts as a catalytic inhibitor of DNA gyrase and therefore represents a new structural type of catalytic inhibitor of DNA gyrase.
The preparation of two, preclinical amino-quinazolinediones as antibacterial agents
Beylin, Vladimir,Boyles, David C.,Curran, Timothy T.,Macikenas, Dainius,Parlett IV, Roger V.,Vrieze, Derek
, p. 441 - 449 (2012/12/31)
This paper describes the synthesis of two amino-quinazolinediones which are potent gyrase/topoisomerase inhibitors and useful as antibacterial agents. The early scale-up work to prepare a chiral side chain on multigram scale and two different amino-quinaz
CYCLIC AMINE COMPOUND
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Page/Page column 110, (2010/11/25)
A compound represented by the formula (I) or a salt thereof: (I) wherein the ring A represents a 5- to 8-membered ring which may have additional substituent besides R6, R7 and R8; R1 represents an electron-attracting group; R2, R3, R4 and R5 independently represent a hydrogen atom, a halogen atom, a group attached through a carbon atom, a group attached through a nitrogen atom, a group attached through an oxygen group, or a group attached through a sulfur atom; R6 represents a halogen atom, a group attached through a carbon atom, a group attached through a nitrogen atom, a group attached through an oxygen group, or a group attached through a sulfur atom, and R7 represents a cyano group, a nitro group, an acyl group which may have a substituent, a carboxyl group which may be esterified or amidated, or a hydrocarbon group which may have a substituent, or R6 and R7 together with a carbon atom to which they are attached may form a ring which may have a substituent; and R8 represents a hydrogen atom, a halogen atom, a group attached through a carbon atom, a group attached through an oxygen atom, or a group attached through a sulfur atom. The compound or salt has an excellent androgen receptor modulating effect, and is useful for the prevention/treatment of hypogonadism, partial androgen deficiency in aging male, decline in physical strength, cachexia, osteoporosis and the like.
A facile synthesis of substituted 3-amino-1H-quinazoline-2,4-diones
Tran, Tuan P.,Ellsworth, Edmund L.,Watson, Brian M.,Sanchez, Joseph P.,Showalter, H. D. Hollis,Rubin, John R.,Stier, Michael A.,Yip, Judy,Nguyen, Dai Q.,Bird, Paul,Singh, Rajeshwar
, p. 669 - 674 (2007/10/03)
A new synthesis of a series of 3-amino-1H-quinazoline-2,4-diones is described. The 1H-quinazoline-2,4-dione 10 was made starting with fluorobenzoic acid in three high yielding steps. The key step of this synthesis involved the generation of the dianion of
Quinoline-3-carboxylic acid derivatives
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, (2008/06/13)
Compounds of formula (I): STR1 (in which R1 is alkoxy, R is alkyl, haloalkyl, alkylamino, cycloalkyl or optionally substituted phenyl, X is chlorine or fluorine and Y is selected from certain specific heterocycles) have excellent antibacterial activity. They may be prepared by introducing the group represented by Y into the corresponding compound in which Y is replaced by a halogen atom.
8-alkoxyquinolonecarboxylic acid and salts thereof
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, (2008/06/13)
Quinolonecarboxylic acid derivatives of the following formula: STR1 wherein R indicates a hydrogen atom or lower alkyl group, R1 indicates a lower alkyl group, R2 indicates a hydrogen atom, amino group or nitro group, X indicates a halogen atom, and Z indicates a halogen atom, piperazino group, N-methylpiperazino group, 3-methylpiperazino group, 3-hydroxypyrrolidino group, or pyrrolidino group of the following formula, STR2 (here, n is 0 or 1, R3 indicates a hydrogen atom or lower alkyl group, R4 indicates a hydrogen atom, lower alkyl group and R5 indicates a hydrogen atom, lower alkyl group, acyl group or alkoxycarbonyl group), the hydrates and pharmaceutically acceptable salts thereof are useful as antibacterial agents.
