A General and Convenient Synthesis of 2h-1,4-Benzoxazin-3(4h)-Ones

Shridhar, D. R.; Jogibhukta, M.; Krishnan, V.

doi:10.1080/00304948209354904

Cited by 24 publications

(1 citation statement)

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“…A flexible synthetic strategy that allowed for facile substitutions at the 1-and 3-positions of 5 is shown in Scheme 1. Compounds 6 12 and 7 13 were prepared from methods described in the literature, followed by alkylation at nitrogen by treatment with an aldehyde and sodium cyanoborohydride. Reduction of the nitro group to the corresponding aniline (9) was followed by treatment with 4,4,4-trifluoroacetoacetate in refluxing benzene, followed by treatment of the crude acetanilide with strong acid, either polyphosphoric acid (PPA) or concentrated H 2 SO 4 (Knorr reaction), 14 to afford the desired 4-substituted-7H- [1,4]oxazino[3,2-g]quinolin-7-one (10).…”

Section: Chemistrymentioning

confidence: 99%

Novel Series of Potent, Nonsteroidal, Selective Androgen Receptor Modulators Based on 7H-[1,4]Oxazino[3,2-g]quinolin-7-ones

et al. 2007

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Recent interest in orally available androgens has fueled the search for new androgens for use in hormone replacement therapy and as anabolic agents. In pursuit of this, we have discovered a series of novel androgen receptor modulators derived from 7H-[1,4]oxazino[3,2-g]quinolin-7-ones. These compounds were synthesized and evaluated in competitive binding assays and an androgen receptor transcriptional activation assay. A number of compounds from the series demonstrated single-digit nanomolar agonist activity in vitro. In addition, lead compound (R)-16e was orally active in established rodent models that measure androgenic and anabolic properties of these agents. In this assay, (R)-16e demonstrated full efficacy in muscle and only partially stimulated the prostate at 100 mg/kg. These data suggest that these compounds may be utilized as selective androgen receptor modulators or SARMs. This series represents a novel class of compounds for use in androgen replacement therapy.

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Section: Chemistrymentioning

confidence: 99%

Novel Series of Potent, Nonsteroidal, Selective Androgen Receptor Modulators Based on 7H-[1,4]Oxazino[3,2-g]quinolin-7-ones

et al. 2007

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Synthesis and herbicidal activity of 1,4-benzoxazin-3-one sulfonylureas

Anderson¹,

Bell²,

Best³

et al. 1996

Pestic. Sci.

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A series of 1,4-benzoxazin-3-ones with a sulfonylurea group attached at either the 5 or 8 position have been synthesised and found to show moderate herbicidal activity. Similarly, a series of 1,4-benzothiazin-3-ones, including some of the related S-oxides and S-dioxides, with a sulfonylurea group linked a t the 8 position, have been prepared and been found to be herbicidal. In both series of compounds many substituent variations were made but none of the compounds showed any useful crop selectivities.

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