.beta.-Adrenergic blocking agents of the chromone and xanthone groups. II. Propanolol type derivatives

Abstract

Notes irradiation of 5-10 g of trans-zearalanol (3a or 3b)# was purified by column chromatography on 200 g of SilicAR, CC-7, with 3% methanol-chloroform to give cis-zearalenol (4a or 4b) as a white amorphous solid,** mp (4a) 124-128°, mp (4b) 126-131°. Anal.(C18H240 5)C, H. Uterotropic Assays. Stock solutions prepared in methanol were diluted and poured on small animal ration (Allied Mills), which was allowed to dry overnight at room temperature. Each test diet was further mixed in a high-speed blender for 1 min before being offered to eight adult castrate female mice for 5 days at 3 g per mouse per day. On day six the animals were sacrificed, and uteri were removed and weighed.Acknowledgment. The author is grateful to Mr. Harold Burns for technical assistance, Mr. Carl Power for performing the uterotropic assays, and Mr. Bill Boyll for carrying

Xanthone Derivatives: New Insights in Biological Activities

“…To this end, the structure-activity relationship (SAR) studies are currently available for the following activities: tuberculostatic [16,[85][86][87], antimycotic [88], antimalarial [89,90], antiplatelet [91][92][93][94], antithrombotic [95], antiinflammatory [54,96,97], antiallergic [13,22,24], antitumor [7,17,81,[98][99][100][101][102][103][104][105][106][107], antimutagenic [108][109][110], and antioxidant [38,43,55]. Furthermore, SAR studies have been also developed in the field of adrenergic blocking agents [7,11] [112], leukotriene (LT) B4 receptors blocking agents [113][114][115], as well as for effects on several enzymes, such as acetylcholinesterase [116,117], aldose reductase [118], aromatase …”

“…(3)) will be highlighted due to their well-recognized and specific mode of action. These include DMXAA (2), psorospermin (12) and AH6809 (11). On the other hand, the use of some xanthone containing extracts in traditional medicine makes imperative to have a detailed discussion of some xanthones such as mangiferin (13), norathyriol (14), α-mangostin (16) and the related prenyl xanthones (17)(18)(19), as well as their effects on mammalian cellular systems.…”

“…Further examination of this activity led to the report of a remarkable central nervous system (CNS) stimulating effect of mangiferin [8], and in vitro experiments have shown that the above effect was caused by an inhibition of the enzyme monoamine oxidase (MAO) [9]. Meanwhile, in a continuing study with aminoalkylxanthones, new aminopropanoxy derivatives were described in 1972 as β-adrenergic blocking agents [10,11]. In the same year, xanthone derivatives developed by isosteric substitution of benzo [b]acronycine were investigated for their in vivo antitumor activity [12], while xanthone-2-carboxylic acids were shown to be effective in allergy [13].…”

New Aloperine–Isoflavone Conjugates

“…Derivatives of phenylpropanolamine and phenoxypropanolamine are typical E-adrenoreceptor blockers [1, 2]. Chromone and flavone derivatives containing a propanolamine fragment are also known to be capable of blocking E-adrenoreceptors [3,4]. Furthermore, several 7-(3-amino-2-hydroxypropoxy) flavonoid derivatives exhibited antihypertensive [5][6][7], antihyperglycemic [8], and antiproliferative [9] activity.…”

“…Their cyclic system can be opened highly regioselectively by N-nucleophiles. Thus, the most common method for synthesizing phenol glycidyl ethers uses attack of the phenols at the oxirane ring of 1-chloro-2,3-epoxypropane (epichlorohydrin) to give the chlorohydrin ethers followed by dehydrochlorination by base to close the epoxide ring [4,5,26,27]. …”