A Convenient One-Step Synthesis of 3-Aryl-2<i>H</i>-1,4-benzoxazines

Shridhar, D. R.; Sastry, C. V. R.; Bansal, O. P.; Rao, P. Pulla

doi:10.1055/s-1981-29648

Cited by 13 publications

(7 citation statements)

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“…1) and their cytotoxicity activity were tested against HepG2 hypoxic and normoxic cell. The 2 H -benzo[ b ][1,4] oxazines were synthesized by modifying the existing methods 12. To a solution of 2-aminophenol (A) (0.001 mol) in dichloromethane (40 mL) aqueous potassium carbonate (20% w/v) and tetrabutylammonium hydrogen sulfate (0.0005 mol) was added and mixture was stirred for 2 h at room temperature.…”

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confidence: 99%

Design, synthesis and biological evaluation of 2H-benzo[b][1,4] oxazine derivatives as hypoxia targeted compounds for cancer therapeutics

Das

Madhukumar

Anguiano

et al. 2009

Bioorganic & Medicinal Chemistry Letters

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A small library of 2H-benzo[b][1,4] oxazine derivative was synthesized and their biological activity was tested on HepG2 cells under normoxic and hypoxic conditions. From preliminary screening, we found compound 10 and 11 specifically inhibit hypoxic cancer cell growth IC50 87 ± 1.8 μM and IC50 10 ± 3.7 μM while sparing ‘normoxic’ cells IC50 >600 M and >1 mM (not applicable), respectively. We tested the effect of 10 on MTT, clonogenic and hypoxia induced genes. The MTT correlates with clonogenic assays and most importantly compound 10 down regulates hypoxia induces genes (HIF-1α, P21 and VEGF) appropriately. We are in the process to explore the molecular mechanism of action of oxazine derivative compounds on hypoxia tumor cells.

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confidence: 99%

Design, synthesis and biological evaluation of 2H-benzo[b][1,4] oxazine derivatives as hypoxia targeted compounds for cancer therapeutics

Das

Madhukumar

Anguiano

et al. 2009

Bioorganic & Medicinal Chemistry Letters

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“…8 and Table 1) 33 : The 2H-benzo[b][1,4] oxazines were synthesized by modifying the existing methods 43 . 2-bromo-4-chloroacetophenone (0.01mol) in dichloromethane was added drop-wise to a solution of 2-aminophenol in dichloromethane, aqueous potassium carbonate (20% w/v) and tetrabutylammonium hydrogen sulphate (0.0005 mol).…”

Section: Methodsmentioning

confidence: 99%

Chemical modulation of chaperone-mediated autophagy by retinoic acid derivatives

et al. 2013

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Chaperone-mediated autophagy (CMA) contributes to cellular quality control and the cellular response to stress through the selective degradation of cytosolic proteins in lysosomes. Decrease in CMA activity occurs in aging and in age-related disorders (for example, neurodegenerative diseases and diabetes). Although prevention of this age-dependent decline through genetic manipulation in mouse has proven beneficial, chemical modulation of CMA is not currently possible, due in part to the lack of information on the signaling mechanisms that modulate this pathway. In this work, we report that signaling through the retinoic acid receptor alpha (RARα) inhibits CMA and apply structure-based chemical design to develop synthetic derivatives of all-trans-retinoic acid (ATRA) to specifically neutralize this inhibitory effect. We demonstrate that chemical enhancement of CMA protects cells from oxidative stress and from proteotoxicity, supporting a potential therapeutic opportunity when reduced CMA contributes to cellular dysfunction and disease.

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“…Their structural elements seem to occur only rarely in lignins (Hwang & Sakakibara, 1981). In connection with some other natural and synthetic work on biologically active neolignan derivatives (Barata et al, 2000), we became interested in the preparation of C-7 nitrogen analogues of 3 0 ,7-epoxy-8,4 0 -oxyneolignans, such as compound (II), previously obtained in moderate yields (Shridhar et al, 1981;Sabitha & Rao, 1987). Compounds with the 2H-benz [b] [1,4]oxazine system have been synthesized in an attempt to obtain anti-inflammatory, central muscle relaxant, diuretic, antibacterial, anti-amoebic, antitrichomonal and anthelmintic agents (Shridhar et al, 1986).…”

Section: Commentmentioning

confidence: 99%