27320-99-6Relevant academic research and scientific papers
Synthesis and Herbicidal Activity of Pyrido[2,3-d]pyrimidine-2,4-dione-Benzoxazinone Hybrids as Protoporphyrinogen Oxidase Inhibitors
Wang, Da-Wei,Li, Qian,Wen, Kai,Ismail, Ismail,Liu, Dan-Dan,Niu, Cong-Wei,Wen, Xin,Yang, Guang-Fu,Xi, Zhen
, p. 5278 - 5286 (2017/07/12)
To search for new protoporphyrinogen oxidase (PPO, EC 1.3.3.4) inhibitors with improved bioactivity, a series of novel pyrido[2,3-d]pyrimidine-2,4-dione-benzoxazinone hybrids, 9-13, were designed and synthesized. Several compounds with improved tobacco PP
Development of small-molecule Trypanosoma brucei N-myristoyltransferase inhibitors: Discovery and optimisation of a novel binding mode
Spinks, Daniel,Smith, Victoria,Thompson, Stephen,Robinson, David A.,Luksch, Torsten,Smith, Alasdair,Torrie, Leah S.,McElroy, Stuart,Stojanovski, Laste,Norval, Suzanne,Collie, Iain T.,Hallyburton, Irene,Rao, Bhavya,Brand, Stephen,Brenk, Ruth,Frearson, Julie A.,Read, Kevin D.,Wyatt, Paul G.,Gilbert, Ian H.
, p. 1821 - 1836 (2015/11/10)
The enzyme N-myristoyltransferase (NMT) from Trypanosoma brucei has been validated both chemically and biologically as a potential drug target for human African trypanosomiasis. We previously reported the development of some very potent compounds based around a pyrazole sulfonamide series, derived from a high-throughput screen. Herein we describe work around thiazolidinone and benzomorpholine scaffolds that were also identified in the screen. An X-ray crystal structure of the thiazolidinone hit in Leishmania major NMT showed the compound bound in the previously reported active site, utilising a novel binding mode. This provides potential for further optimisation. The benzomorpholinone was also found to bind in a similar region. Using an X-ray crystallography/structure-based design approach, the benzomorpholinone series was further optimised, increasing activity against T. brucei NMT by >1000-fold. A series of trypanocidal compounds were identified with suitable in vitro DMPK properties, including CNS exposure for further development. Further work is required to increase selectivity over the human NMT isoform and activity against T. brucei. HATs off to diversity! Screening a diverse library against Trypanosoma brucei N-myristoyltransferase (NMT) identified hits based on thiazolidinone and benzomorpholine scaffolds. X-ray crystallography of these compounds bound to Leishmania major NMT revealed novel active site binding conformations. Using the structural information, the benzomorpholine scaffold was optimised to a blood-brain barrier penetrant compound with activity against TbNMT of 0.002 μm.
Microwave-assisted synthesis of benzo-[1,4]-oxazinones using MeO-PEG-OMe as solvent
Lim, Jae-Min,Gam, Gyunghee,Kim, Shin-Hyuong,Shin, Dong-Soo,Jang, Kiwan
, p. 468 - 472,5 (2020/08/31)
Efficient one-pot microwave-assisted synthesis of various benzo-[1,4]-oxazinones via Smiles rearrangement is described. Treatment of 2-chloroacetamide, substituted 2-chlorophenols and cesium carbonate in MeO-PEG-OMe (2,000) as solvent afforded the corresp
MONOCYCLIC AND BICYCLIC COMPOUNDS AND METHODS OF USE
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Page/Page column 76, (2010/11/26)
Compounds are provided that act as potent antagonists of the CCR1 receptor, and have in vivo anti-inflammatory activity. The compounds are generally monocyclic and bicyclic compounds and are useful in pharmaceutical compositions, methods for the treatment of CCR1-mediated diseases, and as controls in assays for the identification of competitive CCR1 antagonists.
Electrochemical reduction of o-nitrophenoxy compounds: an access to 2H-1,4-benzoxazine derivatives
Mouats, Chabane,Hazard, Roland,Raoult, Eugene,Tallec, Andre
, p. 71 - 77 (2007/10/02)
The electrochemical behavior of o-nitrophenoxyacetophenone, o-nitrophenoxyacetic acid and some related compounds (methyl ester, amide, nitrile) has been investigated in protic media.Controlled potential reductions allow the preparation of 2H-1,4-benzoxazine derivatives from the cyclization of the corresponding phenylhydroxylamines, but the latter can also disproportionate.In some cases, a retrocyclization was observed in warm acidic media, followed by a rearrangement of the parent phenylhydroxylamine. controlled potential electroreductions / 2H-1,4-benzoxazines / cyclic hydroxamic acid / lactam
REACTION OF 7-SUBSTITUTED 4-HYDROXYL-1,4-BENZOXAZIN-3-ONES IN STRONGLY ACIDIC MEDIA
Quiroz, Andres,Niemeyer, Hermann M.
, p. 1681 - 1685 (2007/10/02)
Kinetic and product studies of the reaction of 7-substituted 4-hydroxyl-1,4-benzoxazin-3-ones in strongly acidic media produced biphasic Hammett plots which indicated the intermediacy of a highly elctrophilic nitrogen compound with nitrenium ion character.
Potential Diuretics: Part I - Synthesis of Some Substituted 2,4-Dihydro-1-oxo/thioxotriazolobenzoxazines, Novel Diuretic Agents
Shridhar, D. R.,Jogibhukta, M.,Krishnan, V. S. H.,Joshi, P. P.,Naidu, M. U. R.,et al.
, p. 1279 - 1283 (2007/10/02)
Several compounds (V) derived from 2,4-dihydro-1-oxobenzoxazine and some of their 1-thioxo analogues (VI) have been synthesized and evaluated for their diuretic activity in rats.Compound Vg is the most potent member of this series with 250percent urine output of the saline control at 1 mg/kg dose.The pattern of excretion of electrolytes is similar to that of the hydrochlorothiazide at the same dose.Furthermore, its diuretic activity is very much dose-dependent over a wide range of doses (1.0-32.0 mg/kg).
The Electrochemical Synthesis of Cyclic Hydroxamic Acids Followed by Bamberger Rearrangement
Matschiner, H.,Tanneberg, H.,Maschmeier, C.-P.
, p. 924 - 926 (2007/10/02)
The electrochemical reduction of 2-(o-nitro-phenylthio)acetic acid 1a results in the expected cyclic hydroxamic acid 3a and a rearranged product 4a by consuming 4 electrons.The analogous reduction of 2-(o-nitro-phenoxy)acetic acid 1b leads only to a rearr
