Dataset Information

2-Chloro-3-(4-chloro-benzamido)-1,4-naphthoquinone.

ABSTRACT: The naphthoquinone ring is almost perpendicular [dihedral angle 71.02?(3)°] to the phenyl group of the title compound, C(17)H(9)Cl(2)NO(3), while the dihedral angle between the amide group and the 4-chloro-phenyl ring is 21.9?(2)°. The conformation of the N-H and C=O bonds are anti to each other. N-H?Cl hydrogen bonds link the mol-ecules into chains in the a-axis direction. In addition, these chains are linked by weak inter-molecular C-H?O inter-actions.

SUBMITTER: Brandy Y

PROVIDER: S-EPMC2967976 | biostudies-literature | 2008

REPOSITORIES: biostudies-literature

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2-Chloro-3-(4-chloro-benzamido)-1,4-naphthoquinone.

Brandy Yakini Y Butcher Ray J RJ Adesiyun Tolulope A TA Berhe Solomon S Bakare Oladapo O

Acta crystallographica. Section E, Structure reports online 20081210 Pt 1

The naphthoquinone ring is almost perpendicular [dihedral angle 71.02 (3)°] to the phenyl group of the title compound, C(17)H(9)Cl(2)NO(3), while the dihedral angle between the amide group and the 4-chloro-phenyl ring is 21.9 (2)°. The conformation of the N-H and C=O bonds are anti to each other. N-H⋯Cl hydrogen bonds link the mol-ecules into chains in the a-axis direction. In addition, these chains are linked by weak inter-molecular C-H⋯O inter-actions. ...[more]

PMID: 21581704

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Project description:BACKGROUND AND PURPOSE: 1,4-Naphthoquinones exhibit antiplatelet activity both in vivo and in vitro. In the present study, we investigated the antiplatelet effect of a novel naphthoquinone derivative NP-313, 2-acetylamino-3-chloro-1,4-naphthoquinone and its mechanism of action. EXPERIMENTAL APPROACH: We measured platelet aggregation, Ca(2+) mobilization, thromboxane B2 formation and P-selectin expression and examined several enzymatic activities. Furthermore, we used the irradiated mesenteric venules in fluorescein sodium-treated mice to monitor the antithrombotic effect of NP-313 in vivo. KEY RESULTS: NP-313 concentration-dependently inhibited human platelet aggregation induced by collagen, arachidonic acid, thapsigargin, thrombin and A23187. NP-313 also inhibited P-selectin expression, thromboxane B(2) formation and [Ca(2+) ](i) elevation in platelets stimulated by thrombin and collagen. NP-313 at 10 µM inhibited cyclooxygenase, thromboxane A(2) synthase, and protein kinase C?, whereas it did not affect phospholipase A(2) or phospholipase C activity. In the presence of indomethacin and an adenosine 5-diphosphate scavenger, NP-313 concentration-dependently inhibited thrombin- and A23187-induced [Ca(2+)](i) increase through its inhibitory effects on Ca(2+) influx, rather than blocking Ca(2+) release from intracellular stores. NP-313 also inhibited thapsigargin-mediated Ca(2+) influx through store-operated calcium channel but had no effect on Ca(2+) influx through store-independent calcium channel evoked by the diacylglycerol analogue 1-oleoyl-2-acetyl-sn-glycerol. Nevertheless, it had little effect on cyclic AMP and cyclic GMP levels. Also, intravenously administered NP-313 dose-dependently inhibited the thrombus occlusion of the irradiated mesenteric vessels of fluorescein-pretreated mice. CONCLUSIONS AND IMPLICATIONS: Taken together, these results indicate that NP-313 exerts its antithrombotic activity through dual inhibition of thromboxane A(2) synthesis and Ca(2+) influx through SOCC.

Dataset Information

2-Chloro-3-(4-chloro-benzamido)-1,4-naphthoquinone.

Publications

2-Chloro-3-(4-chloro-benzamido)-1,4-naphthoquinone.

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