Experiments with substituted (3,2-c)-pyranyl-2, 10-diones and benzopyranyl-(3,2-c) pyran-2,8-diones

Mustafa, Ahmed; Hsihmat, O.H.; Zayed, S. M. A. D.; Nawar, A. A.

doi:10.1016/s0040-4020(01)99257-9

Cited by 21 publications

(7 citation statements)

References 27 publications

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“…1,2-Benzisoxazole-3-acetic acid (1) was prepared according to the published procedure 25 in 46% yield: mp 120-125 °C (lit. 25 mp 125 °C); TLC Rf ) 0.50 in EtOAc/hexane (1:1) with 1% acetic acid; 1 H NMR (CDCl3/DMSO-d6, 8:1) δ 3.93 (s, 2H), 7.22-7.26 (m, 1H), 7.44-7.49 (m, 2H), 7.67 (d, J ) 7.9 Hz, 1H).…”

Section: Methodsmentioning

confidence: 99%

1,2-Benzisoxazole Phosphorodiamidates as Novel Anticancer Prodrugs Requiring Bioreductive Activation

Jain

Kwon

2003

J. Med. Chem.

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Several 1,2-benzisoxazole phosphorodiamidates have been designed as prodrugs of phosphoramide mustard requiring bioreductive activation. Enzymatic reduction of 1,2-benziosoxazole moiety is expected to result in the formation of imine intermediate due to the cleavage of the N-O bond. The imine should then be spontaneously hydrolyzed to a ketone metabolite, thereby facilitating base-catalyzed beta-elimination of cytotoxic phosphoramide mustard. As expected, the proposed prodrugs 4, 9, and 12 were at least 3-5-fold more potent cytotoxins than control compounds 5 and 15, which lack in the phosphoramide mustard group. Upon incubation with phenobarb-induced rat liver S-9 fraction, compounds 4, 9, and 12 underwent extensive NADPH-dependent metabolism with concomitant generation of alkylating activity under both hypoxic and oxic conditions. Corresponding ketone metabolites were detected for 9 and 15. NADPH-dependent bioreduction of 15 to its ketone metabolite 16 was located in the microsomal fraction and inhibited by SKF-525A and pCMBA. Compared with phenobarb-induced rat liver microsomal fraction, incubation of 15 with rat or human p450 reductase microsomes showed moderate generation of 16. Microsomal cytochrome p450 and/or p450 reductase appear to be involved in the reductive metabolism of 1,2-benzisoxazole moiety under hypoxic as well as oxic conditions.

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Section: Methodsmentioning

confidence: 99%

1,2-Benzisoxazole Phosphorodiamidates as Novel Anticancer Prodrugs Requiring Bioreductive Activation

Jain

Kwon

2003

J. Med. Chem.

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“…有关香豆素并吡喃酮类化合物的合成, 在早期合成方法中介绍了在硫酸作用下, 通过 3-苯乙酰酰基(或乙酰乙酰基)-4-羟基香豆素的环化得到香豆素并 [4,3-b] 吡喃-4-酮类衍生物 [6] , 但该方法受到原料来源的限制.…”

Section: 吡喃-4-酮类化合物由于良好的抗菌unclassified

“…5,108.0,112.0,113.6,117.2,124.8,125.4,126.6,127.4,130.3,135.7,142.8,153.7,155.8,161.2,164.9,174.4;IR (KBr) 20.7,107.3,113.1,116.6,116.8,123.8,124.9,127.0,127.6,129.3,131.9,135.2,136.4,141.1,153.2,155.3,162.9,164.8,173.7;IR (KBr) 2,107.9,112.5,113.2,117.5,123.7,125.0,125.9,126.5,127.1,135.4,153.9,156.1,156.3,161.9,164.8,174.5;IR (KBr) MHz) δ: 107. 6,112.7,113.0,116.7,124.3,124.8,…”

Section: 香豆素并[43-b]吡喃-4-酮类衍生物的合成mentioning

confidence: 99%

Synthesis of Coumarino[4,3-b]pyran-4-one Derivatives

王道林¹,

杨菲菲²,

刘忠³

et al. 2014

Chin. J. Org. Chem.

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An efficient and easy method for the synthesis of coumarino [4,3-b]pyran-4-one derivatives underwent oxidative cyclization of 3-cinnamoyl-4-hydroxycoumarins, synthesized from condensation between 3-acetyl-4-hydroxycoumarin and aromatic aldehydes in the presence of piperidine and PEG-400 by using iodine in DMSO, has been described. All of above compounds have been confirmed by NMR, IR, MS spectra and elemental analysis.

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“…Examples of annulation of the pyrone ring in coumarin derivatives are also known [6,7]. For example, 4-hydroxy-3-propionyl-and 4-hydroxy-3-phenylacetylcoumarins undergo annulation with the formation of new γ-pyrone rings when heated with acetic anhydride in the presence of sodium acetate.…”

mentioning

confidence: 99%

“…In the case of enolization of the acetyl group in compound 7 the formation of the γ-pyrone derivatives 8 as final products should be expected, but they were not detected even in trace quantities (scheme 2 In order to confirm scheme 1 compound 4a was prepared by an alternative method [6]. The obtained ester 7 is enolized at the ester group.…”

mentioning

confidence: 99%