- Direct synthesis of benzoxazinones via Cp*Co(III)-catalyzed C–H activation and annulation of sulfoxonium ylides with dioxazolones
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A highly novel and direct synthesis of benzoxazinones was developed via Cp*Co(III)-catalyzed C–H activation and [3 + 3] annulation between sulfoxonium ylides and dioxazolones. The reaction is conducted under base-free conditions and tolerates various functional groups. Starting from diverse readily available sulfoxonium ylides and dioxazolones, a variety of benzoxazinones could be synthesized in one step in 32%-75% yields.
- Yu, Yongqi,Xia, Zhen,Wu, Qianlong,Liu, Da,Yu, Lin,Xiao, Yuanjiu,Tan, Ze,Deng, Wei,Zhu, Gangguo
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p. 1263 - 1266
(2020/10/08)
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- Palladium (0)-catalyzed C(sp2)-H oxygenation with carboxylic acids
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Palladium (0)-catalyzed Ortho-benzoxylation of the sp2 C–H bond of arylbenzoxazinones with carboxylic acid is reported. With benzoxazinone as directing group, the reaction went smoothly under the benign condition and gave the desired product wi
- Gong, Ai-Jun,Li, Xu-Qin,Vu, Huu-Manh,Yong, Jia-Yuan
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supporting information
(2020/02/15)
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- Palladium-Catalyzed C-H Bond Monofluorination of 2-Arylbenzo[ d ]oxazinone Using Nitrate as Crucial Promoter
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Monofluorination of 2-arylbenzo[ d ]oxazinones with N -fluorobenzenesulfonimide (NFSI) was achieved by palladium catalysis in moderate to good yields. Promoted by nitrate, the reaction provides an economic and environmentally friendly strategy. The synthesis of monofluorinated 2-arylbenzo[ d ]oxazinones has good compatibility with many common functional groups. The plausible mechanism of this monofluorination is discussed.
- Vu, Huu-Manh,Li, Xu-Qin,Chen, Fei-Wu
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p. 1578 - 1584
(2019/03/26)
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- Discovery and validation of 2-styryl substituted benzoxazin-4-ones as a novel scaffold for rhomboid protease inhibitors
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Rhomboids are intramembrane serine proteases with diverse physiological functions in organisms ranging from archaea to humans. Crystal structure analysis has provided a detailed understanding of the catalytic mechanism, and rhomboids have been implicated in various disease contexts. Unfortunately, the design of specific rhomboid inhibitors has lagged behind, and previously described small molecule inhibitors displayed insufficient potency and/or selectivity. Using a computer-aided approach, we focused on the discovery of novel scaffolds with reduced liabilities and the possibility for broad structural variations. Docking studies with the E. coli rhomboid GlpG indicated that 2-styryl substituted benzoxazinones might comprise novel rhomboid inhibitors. Protease in vitro assays confirmed activity of 2-styryl substituted benzoxazinones against GlpG but not against the soluble serine protease α-chymotrypsin. Furthermore, mass spectrometry analysis demonstrated covalent modification of the catalytic residue Ser201, corroborating the predicted mechanism of inhibition and the formation of an acyl enzyme intermediate. In conclusion, 2-styryl substituted benzoxazinones are a novel rhomboid inhibitor scaffold with ample opportunity for optimization.
- Goel, Parul,Jumpertz, Thorsten,Tichá, Ane?ka,Ogorek, Isabella,Mikles, David C.,Hubalek, Martin,Pietrzik, Claus U.,Strisovsky, Kvido,Schmidt, Boris,Weggen, Sascha
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supporting information
p. 1417 - 1422
(2018/02/21)
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- Silver and Palladium Cocatalyzed Carbonylative Activation of Benzotriazoles to Benzoxazinones under Neutral Conditions
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A novel and efficient method for the carbonylative activation of benzotriazoles to benzoxazinones has been developed. By using a silver and palladium bimetallic catalyst system, a broad range of benzotriazoles were transformed into the corresponding benzoxazinones in moderate to good yields with excellent functional group tolerance. Notably, this procedure proceeds under neutral conditions.
- Yin, Zhiping,Wang, Zechao,Wu, Xiao-Feng
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supporting information
p. 6232 - 6235
(2017/11/24)
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- BCL-3 INHIBITORS
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The present application relates to compounds of any one of Formulae I, Ia, Ib, Ic, Id, Ie, and If. Compounds of Formula (I) have the structure, wherein A, B, Y, Z, R2, R4, R5, R6, Rq and q are as defined herein. The compounds can be used as inhibitors of Bcl-3 and can be used for the treatment of cancer, particularly metastatic cancer.
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Paragraph 000366; 000367; 000368; 000383; 000384
(2016/04/06)
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- 2-BENZOYLAMINOBENZAMIDE DERIVATIVES AS BCL-3 INHIBITORS
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The invention relates to a compound of general formula (I): wherein R1, R2, R3, R4, Q, m and n are as defined herein. The compounds are inhibitors of Bcl3 and are useful for the treatment of cancer, particularly
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Page/Page column 25; 26
(2015/02/25)
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- One-pot approach to 2-arylbenzoxazinone derivatives from 2-alkynylanilines using copper-mediated tandem reactions
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In this study, we describe a one-pot method to obtain a variety of 2-arylbenzoxazinones and N-benzoyl anthranilic acid by using a copper catalyst and molecular oxygen as oxidants. This protocol involves tandem cyclization and oxidative processes of 2-alkynylanilines to afford significant motifs in synthetic and medicinal chemistry with moderate yields. We also demonstrated that combining the Sonogashira coupling and the developed method realized the synthesis of 2-arylbenzoxazinones derivatives from commercially available 2-iodoanilines and terminal acetylenes.
- Yamashita, Mitsuaki,Iida, Akira
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p. 5746 - 5751
(2015/03/30)
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- Copper-mediated oxidative tandem reactions with molecular oxygen: Synthesis of 2-arylbenzoxazinone derivatives from indoles
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We developed an efficient method for the transformation of indoles by utilizing a copper catalyst and molecular oxygen as the oxidant. The transformation involves a tandem oxidative process of 2-arylindoles. Our reaction afforded a variety of N-benzoyl an
- Yamashita, Mitsuaki,Iida, Akira
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supporting information
p. 2991 - 2993
(2014/05/06)
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- Synthesis of 2-Aryl-4H-3,1-Benzoxazin-4-ones: A Class of α-Chymotrypsin Inhibitors
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Twenty one derivatives of 2-aryl-4H-3,1-benzoxazin-4-one were synthesized and their potential therapeutically significance and structureactivity relationship were tested against α-chymotrypsin. Majority of synthesized compounds showed significant in vitro α-chymotrypsin inhibitory properties having IC50values in the range of 5.42 ± 1.66 - 41.27 ± 1.33 μM, whereas standard inhibitor chymostatin have IC50 value 7.13 ± 1.06 μM. In the present series compounds 2-(2-fluorophenyl)-4H-3,1-benzoxazin-4-one (3h), 2-(2-bromophenyl)-4H-3,1- benzoxazin-4-one (3n) and 2-(1-naphthyl)-4H-3, 1-benzoxazin-4-one (3t) with IC50values 7.22 ± 0.75, 6.99 ± 0.29 and 5.42 ± 1.66 μM, respectively were found to be most active members of series, even better than standard inhibitor a-chymostatin.
- Khan, Zulfiqar Ali,Afzal, Noshaba,Hussain, Zaib,Naqvi, Syed Ali Raza,Bari, Ayesha,Shahzad, Sohail Anjum,Yar, Muhammad,Mahmood, Nasir,Bukhari, Shazia Anwer,Mansha, Asim,Zahoor, Ameer Fawad,Khan, Abdur Rahman,Ahmad, Matloob
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p. 4561 - 4565
(2014/12/10)
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- Facile synthesis and herbicidal evaluation of 2-Aryl-4H-3, 1-benzoxazin-4-ones
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The present work deals with the synthesis of 4H-3,1-benzoxazin-4-ones carrying an aryl functional group at position-2. Synthesized compounds tested for herbicidal activity at three different doses (500 μg/mL, 50 μg/mL and 5μg/mL). Most of the compounds exhibited significant herbicidal activity against Lemna aequinocitalis welv. at higher dose (500 μg/mL). Among the tested compounds 2-phenyl-4H-3,1-benzoxazin-4-one (3a) and 2-(3-chlorophenyl)- 4H-3,1-benzoxazin-4- one (3l) completely inhibited the plant growth at 500 and 50 μg/mL concentrations. All the synthetic compounds were characterized by FT-IR, 1H NMR, EI-MS and elemental analysis.
- Hussain, Zaib,Khan, Zulfiqar Ali,Naqvi, Syed Ali Raza,Shahzad, Sohail Anjum,Yar, Muhammad,Hussain, Abdullah Ijaz,Chatha, Shahzad Ali Shahid,Mahmood, Nasir,Khan, Khalid Mohammed
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p. 449 - 455
(2013/07/27)
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- Synthesis and antimicrobial activity of 2-Aryl-4H-3,1-benzoxazin-4-ones
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Twenty derivatives of 2-aryl-4H-3,1-benzoxazin-4-one synthesized and their potential therapeutically significance tested against two strains of Gram positive bacteria (Staphylococcus aureus and Bacillus subtilis) and four strains of Gram negative bacteria (Shigella flexnari, Escherichia coli, Salmonella typhi and Pseudomonas aeruginsoa) by agar well diffusion method. The 2-(3-nitrophenyl)-4H-3,1-benzoxazin-4-one (3f) recorded significant antibacterial activity against Bacillus subtilis whereas 2-(4-bromophenyl)-4H-3, 1-benzoxazin-one (3o) exhibited weak antibacterial activity against Staphylococcus aureus. Further 2-(2-methylphenyl)-4H-3,1-benzoxazin-4-one (3b) showed significant activity against Shigella Flexnari, Escherichia coli, Pseudomonas aeruginsoa and Salmonella typhi. The antibacterial activity of synthesized derivatives of 2-aryl-4H-3,1-benzoxazin-4-one was compared to reference standard antibiotics amoxycillin, streptomycin, kanamycin and ciprofloxacin. The present study revealed that 2-aryl-4H-3,1-benzoxazin-4-ones possess good bactericidal activity against a panel of bacteria causing common bacterial diseases and therefore opens the possibility of finding latest clinically useful antibacterial compounds. The synthesized compounds were characterized by 1H NMR, EI, FT-IR and elemental analysis.
- Khan, Zulfiqar Ali,Naqvi, Syed Ali Raza,Shahzad, Sohail Anjum,Mahmood, Nasir,Yar, Muhammad,Zahoor, Ameer Fawad
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p. 152 - 156
(2013/02/22)
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- Phl(OAc)2-mediated one-pot synthesis of benzoxazinones from anthranilic acids and aromatic aldehydes
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A novel way to synthesise 2-aryl-4H-benzo[d][1,3]oxazin-4-ones has been developed by the cyclisation of Schiff bases with (diacetoxyiodo)benzene. The salient features of this new protocol which starts from an anthranilic acid and an aromatic aldehyde, are
- Xie, Yuanyuan,Wang, Suping
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experimental part
p. 123 - 126
(2012/09/22)
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- HETEROCYCLIC COMPOUNDS REGULATING CLOTTING
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Compounds of formula (I) as factor VII-tissue factor inhibitors as well as novel benzoxazin derivatives are disclosed, wherein R1, R2, R3, X and Y are as defined in the specification. These compounds, and pharmaceutically acceptable salts thereof, have be
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- Synthesis and evaluation of 2-aryl-4H-3,1-benzoxazin-4-ones as C1r serine protease inhibitors
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A series of 2-aryl-4H-3,1-benzoxazin-4-ones have been synthesized and tested for inhibitory activity against C1r serine protease. Compounds were found that were equipotent and more selective than the reference compound FUT-175.
- Gilmore, John L.,Hays, Sheryl J.,Caprathe, Bradley W.,Lee, Chitase,Emmerling, Mark R.,Michael, Walter,Jaen, Juan C.
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p. 679 - 682
(2007/10/03)
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