70917-44-1Relevant articles and documents
Design, synthesis and antimycobacterial activity of benzoxazinone derivatives and open-ring analogues: Preliminary data and computational analysis
Zampieri, Daniele,Mamolo, Maria Grazia,Filingeri, Julia,Fortuna, Sara,De Logu, Alessandro,Sanna, Adriana,Zanon, Davide
, p. 2468 - 2474 (2019)
This study examines in depth benzoxazine nucleus for antimycobacterial property. We synthesized some benzoxazin-2-one and benzoxazin-3-one derivatives, which were tested for activity against a panel of Mycobacterium tuberculosis (Mtb) strains, including H37Ra, H37Rv and some resistant strains. Several compounds displayed a high antimycobacterial activity and the three isoniazid analogue derivatives 8a-c exhibited a MIC range of 0.125–0.250 μg/mL (0.37–0.75 μM) against strain H37Ra, therefore lower than the isoniazid reference drug. Two benzoxazin-2-one derivatives, 1c and 5j, together with isoniazid-analogue compound 8a, also revealed low MIC values against resistant strains and proved highly selective for mycobacterial cells, compared to mammalian Vero cells. To predict whether molecule 8a is able to interact with the active site of InhA, we docked it into the crystal structure; indeed, during the molecular dynamic simulation the compound never left the protein pocket. The more active compounds were predicted for ADME properties and all proved to be potentially orally active in humans.
Hydroamination reactions of alkynes with ortho-substituted anilines in ball mills: Synthesis of benzannulated N-heterocycles by a cascade reaction
Weisse, Maik,Zille, Markus,Jacob, Katharina,Schmidt, Robert,Stolle, Achim
, p. 6511 - 6522 (2015/04/22)
It was demonstrated that ortho-substituted anilines are prone to undergo hydroamination reactions with diethyl acetylenedicarboxylate in a planetary ball mill. A sequential coupling of the intermolecular hydroamination reaction with intramolecular ring cl
Expedient synthesis of novel 1,4-benzoxazine and butenolide derivatives
Choudhary, Garima,Naganaboina, Ram Tilak,Peddinti, Rama Krishna
, p. 17969 - 17979 (2014/05/20)
A highly efficient and rapid method for the synthesis of 2-hydroxy-1,4-benzoxazine and butenolide derivatives has been developed. The key step in this protocol involves the reduction of benzoxazinone derivatives. Further reaction of 2-hydroxy-1,4-benzoxazine with secondary amines and sodium methoxide affords the corresponding 2-amino-1,4-benzoxazines and butenolide derivatives, respectively, in good yields.
Novel approach for the synthesis of pyrrolo[2,1-c][1,4]benzoxazines and pyrrolo[1,2-A]quinoxalines
Sanaeishoar, Tayebeh,Adibi-Sedeh, Somayeh,Karimian, Saghar
, p. 157 - 161 (2014/03/21)
An efficient synthesis of alkyl 4,5-dihydro-4-oxo-2-phenylpyrrolo[2,1-c][1, 4]benzoxazine-3-carboxylates and alkyl 4,5-dihydro-4-oxo-2-phenylpyrrolo[1,2-A] quinoxaline-3-carboxylates is described. This involves a three-component reaction between o-Aminoph
Introduction of a clean and promising protocol for the synthesis of β-amino-acrylates and 1,4-benzoheterocycles: An emerging innovation
Choudhary, Garima,Peddinti, Rama Krishna
experimental part, p. 3290 - 3299 (2011/12/16)
A highly efficient, elegant and simple procedure with exceptionally mild conditions has been proposed for the synthesis of β-amino-acrylate derivatives and an array of biologically and pharmaceutically active benzoheterocycles. The protocol offers a valua
Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: Novel antibacterial agents against Mycobacterium tuberculosis
Li, Xiaokai,Liu, Nina,Zhang, Huaning,Knudson, Susan E.,Slayden, Richard A.,Tonge, Peter J.
supporting information; experimental part, p. 6306 - 6309 (2010/12/18)
Menaquinone is an essential component of the electron transport chain in many pathogens and consequently enzymes in the menaquinone biosynthesis pathway are potential drug targets for the development of novel antibacterial agents. In order to identify lea
An efficient synthesis of functionalized 6,10-dioxo-6,10-dihydro-5H- pyrido[1,2-a]quinoxalines and 6,10-dioxo-6,10-dihydropyrido[2,1-c][1,4] benzoxazines
Yavari, Issa,Souri, Sanaz,Sirouspour, Mehdi,Bayat, Mohammad J.
body text, p. 1921 - 1922 (2010/03/04)
An efficient synthesis of alkyl 8-hydroxy-6,10-dioxo-6,10-dihydro-5H- pyrido[1,2-a]quinoxaline-7-carboxylates and alkyl 8-hydroxy-6,10-dioxo-6,10- dihydropyrido[2,1-c][1,4]benzoxazine-7-carboxylates is described. This involves the reaction between malonyl dichloride and alkyl 2-[3,4-dihydro-3- oxoquinoxaline 2(1H)-ylidene]acetates or alkyl 2-(2-oxo-2H-benzo[b][1,4]oxazin- 3(4H)-ylidene)acetates in CH2Cl2 at room temperature. Georg Thieme Verlag Stuttgart.
Structural Elucidation of the Reaction Products of Benzoxazole Derivatives with Dimethyl Acetylenedicarboxylate. V
Kawahara, Norio,Nakajima, Takako,Itoh, Tsuneo,Takayanagi, Hiroaki,Ogura, Haruo
, p. 1163 - 1169 (2007/10/02)
Benzoxazole and o-aminophenol each reacted with dimethyl acetylenedicarboxylate (DMAD) to give the same product, which was previously suggested to be a benzoxazinepyran derivative (2).An X-ray crystallographic analysis has now shown the structure of this compound to be trimethyl 2,3-dihydro-2-oxo-4H-1,4-benzoxazine-Δ3,7-aconitate.A similar treatment of o-aminophenols and β-aminoalcohols with an excess of DMAD afforded new 1,4-benzoxazines and 1,4-oxazines, respectively.Keywords benzoxazole derivative; dimethyl acetylenedicarboxylate; X-ray analysis; o-aminophenol; β-aminoalcohol; 1,4-benzoxazine; 1,4-oxazine
Synthesis and Reactions of Some Novel Imidazobenzoxazines and Related Systems
Danswan, Geoff W.,Hairsine, Peter W.,Rowlands, David A.,Taylor, John B.,Westwood, Robert
, p. 1049 - 1058 (2007/10/02)
A novel synthesis of the new 4H-imidazobenzoxazine system (2) has been carried out under two sets of conditions, leading to products with differing functionalities.The effect of substituents on the cyclization step has been investigated and the reactions of the functional groups of the new ring system have been studied.Derivatives of the related 4,5-dihydroimidazobenzoxazepine (3) have also been prepared.
