Synthesis and anti-ulcer activities of sodium alkylazulene sulfonates.

Yanagisawa, Takashi; Wakabayashi, Shigeru; Tomiyama, T.; Yasunami, Michio; Takase, Kahei

doi:10.1248/cpb.36.641

Cited by 77 publications

(34 citation statements)

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“…In addi- Akagi/Matsui/Mochizuki/Tasaka tion, egualen sodium also exhibited a therapeutic effect against chronic gastritis induced by sodium taurocholate in rats [19]. Although the mechanisms responsible for the antiulcer and antigastrisis effects have been reported to be increased blood flow [8], prevention of vascular injury [5], prevention of decrease of endogenous SH compounds [5], blockade of TXA 2 receptors [9], inhibition of LTC 4 release [10], and antipeptic activity [11], it became clear from the present study that the inhibitory effect of egualen sodium on histamine release from mast cell-like cells also participates in the treatment of gastritis and peptic ulcers.…”

Section: Discussionmentioning

confidence: 99%

“…It was reported that egualen sodium dose-dependently inhibited the development of gastric lesions induced by HCl-ethanol, HCl-aspirin or aspirin, and Shay ulcers, without affecting basal secretions [4][5][6][7]. The mechanisms responsible for the anti-ulcer effect of egualen sodium are reported to increase mucosal blood flow [8], prevent a vascular injury [5], prevent a decrease in endogeneous sulfhydryl (SH) compounds [5], block thromboxane (TX) A 2 receptors [9], inhibit a leukotriene (LT) C 4 release [10], and have an antipeptic activity [11].…”

Section: Introductionmentioning

confidence: 99%

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Inhibitory Effect of Egualen Sodium: A New Stable Derivative of Azulene on Histamine Release from Mast Cell-Like Cells in the Stomach

Akagi

Matsui²,

Mochizuki³

et al. 2001

Pharmacology

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We studied the inhibitory effect of egualen sodium (ES) (sodium 3-ethyl-7-isopropyl-1-azulenesulfonate 1/3 hydrate, KT1–32), a new derivative and more stable compound than azulene, on histamine release from the mucosal histaminocytes and elucidated the mechanism for this action. ES prevented the histamine release from isolated mast cell-like cells of the guinea pig stomach induced by A23187 in a dose-dependent fashion. ES dose-dependently inhibited the histamine release from lung pieces of sensitized guinea pigs induced by an antigen-antibody reaction. ES also inhibited histamine release from rat peritoneal mast cells induced by compound 48/80 or antigen-antibody reaction. ES exhibited the membrane stabilizing activity on DPPC liposomes. These findings suggest that ES may prevent histamine release from histaminocytes induced by various stimuli and the stabilizing action of the cell membrane may be responsible for the inhibition of histamine release.

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Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Inhibitory Effect of Egualen Sodium: A New Stable Derivative of Azulene on Histamine Release from Mast Cell-Like Cells in the Stomach

Akagi

Matsui²,

Mochizuki³

et al. 2001

Pharmacology

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“…The above is in accordance with previous work reporting increased anti-inflammatory activity of azulene-sulphonic acids of comparable lipophilic character with compound 6b. 9) In conclusion, this study indicates that new azulene derivatives with anti-inflammatory and antioxidant activities can be designed, and proposes structural and physicochemical features that contribute to this combination of actions. Further work is in progress, to extend the structural modifications, as well as the evaluation of activity in this series of compounds.…”

Section: Resultsmentioning

confidence: 80%

Synthesis of New Azulene Derivatives and Study of Their Effect on Lipid Peroxidation and Lipoxygenase Activity.

et al. 2002

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The relationship between free radicals and acute or chronic inflammation has been well established. We have previously reported the significant antioxidant activity of the natural azulene derivatives chamazulene and guaiazulene. Furthermore, some synthetic azulene analogues have been found to possess anti-inflammatory activity. In this investigation we report the synthesis of five 3-alkyl or 3-(hydroxy)alkylazulene-1-carboxylic acids and esters, from tropolone, via the corresponding furanone. The synthesised compounds were tested for their effect on the peroxidation of rat hepatic microsomal membrane lipids, applying the 2-thiobarbituric acid test. Their anti-inflammatory activity was evaluated in vitro by the offered inhibition of soybean lipoxygenase. All the tested molecules were found to inhibit lipid peroxidation by 100% at 1 mM. They were also found to considerably inhibit lipoxygenase activity. The above results are discussed in relation to the structure and physicochemical properties of the examined azulene derivatives.

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“…薁类衍生物具有广泛的生物活性, 如抗溃疡 [9] 、抗癌 [10] 、抗氧化 [11] , 以及除草、杀虫、杀菌 24.66,25.19,25.31,37.95,39.89,125.33,127.14,133.36,134.25,135.76,138.78,140.02,141.24,146.45,148.23,161.97,182.92;IR (KBr) 24.51,25.37,25.85,38.05,41.45,59.45,112.92,116.73,122.76,124.43,126.17,126.49,132.38,133.26,135.26,137.75,141.12,141.34,145.35,146.55,147.17,148.37,150.12,160.25,162.68;IR (KBr) 最后, 在优化的反应条件下, 对 1-(2-氨基-3,5-二氰基-4-芳基-4H-吡喃-6-基)愈创兰烃薁衍生物 4a～4k 的合成(Eq. 1)进行实验(表 2).…”

Section: 众所周知 4h-吡喃类化合物是天然产物mentioning

confidence: 99%

Synthesis of 1-(2-Amino-3,5-dicyano-4-aryl-4H-pyran-6-yl)guaiazulenes

王道林¹,

李帝²,

Cao³

2012

Chin. J. Org. Chem.

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An efficient and convenient method for the one-pot three-component synthesis of 1-(2-amino-3,5-dicyano-4-aryl-4H-pyran-6-yl)guaiazulene derivatives by the condensation of 1-cyanoacetylguaiazulene, aldehydes, and malononitrile in the presence of ammonium acetate has been described. The structures of synthesized compounds were determined by NMR, IR, MS techniques and elemental analysis. This method provides several advantages such as good yield and simple work-up procedure.

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Synthesis and anti-ulcer activities of sodium alkylazulene sulfonates.

Cited by 77 publications

References 0 publications

Inhibitory Effect of Egualen Sodium: A New Stable Derivative of Azulene on Histamine Release from Mast Cell-Like Cells in the Stomach

Inhibitory Effect of Egualen Sodium: A New Stable Derivative of Azulene on Histamine Release from Mast Cell-Like Cells in the Stomach

Synthesis of New Azulene Derivatives and Study of Their Effect on Lipid Peroxidation and Lipoxygenase Activity.

Synthesis of 1-(2-Amino-3,5-dicyano-4-aryl-4H-pyran-6-yl)guaiazulenes

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