Derivatives of Benzo[f]quinoline

Blicke, F. F.; Gearien, James E.

doi:10.1021/ja01644a038

Cited by 36 publications

(59 citation statements)

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“…110°C/0.02 mbar (ref. [43] 152Ϫ153°C/ [27] Compound 35 (6.30 g, 23.5 mmol) and water (0.45 g, 25 mmol) were added to a solution of sodium ethoxide [from sodium (0.58 g, 25 mmol) and anhydrous ethanol (12 mL)]. After the mixture was stirred for 5 min, a colorless precipitate had formed, and this was filtered off, washed with diethyl ether, and dried at 60°C.…”

Section: -Benzyl-25-diphenylpyrrole (30b)mentioning

confidence: 99%

Electrocyclization Reactions of 1-Aza- and 1-Oxapentadienyl and -heptatrienyl Cations: Synthesis of Pyrrole and Furan Derivatives

et al. 2002

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Section: -Benzyl-25-diphenylpyrrole (30b)mentioning

confidence: 99%

Electrocyclization Reactions of 1-Aza- and 1-Oxapentadienyl and -heptatrienyl Cations: Synthesis of Pyrrole and Furan Derivatives

et al. 2002

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“…This paper describes the pharmacology of the esters of pyrrolidyl alcohols synthesized by Doyle, Mehta, and Sach (unpublished observations). Of these compounds only the benzilic and diphenylacetic acid esters of 1-methyl-2-hydroxymethylpyrrolidine have previously been reported (Blicke and Lu, 1955). …”

mentioning

confidence: 99%

Pharmacological Properties of Esters of 1‐alkyl‐2‐hydroxyalkylpyrrolidine and Their Quaternary Derivatives

Acred¹,

Atkins²,

Bainbridge³

et al. 1957

British Journal of Pharmacology and Chemotherapy

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A series of esters of l-alkyl-2-hydroxyalkylpyrrolidine and their quaternary derivatives have been shown to possess significant anti-acetylcholine activity. The benzilic acid esters were the most active, followed by xanthene-9-carboxylic acid, fluorene-9-carboxylic acid and diphenylacetic acid esters in that order. The quaternary derivatives were more active than their corresponding tertiary compounds both in vivo and in vitro. The most active compound of the series tested in vivo was (I-methylpyrrolid-2-yl)methyl benzilate methiodide and was as potent as atropine.There was a progressive decrease in anti-acetylcholine activity and a proportional increase in local anaesthetic activity as the number of carbon atoms was increased from 1 to 3 in the pyrrolidyl side-chain of the tertiary salts of the benzilic acid ester series. Likewise increasing the size of the group on the nitrogen atom led to a decrease in anti-acetylcholine activity and an increase in local anaesthetic activity. Quaternization of the tertiary salts resulted in a loss of local anaesthetic activity. Most of the compounds tested possessed some antihistamine properties, while papaverine-like activity was confined to the tertiary salts only. No significant neuromuscular blocking activity was evident.There have been numerous attempts to modify the structure of atropine with a view to minimizing its undesirable side effects, and many simple esters have been prepared which have shown antiacetylcholine activity. This paper describes the pharmacology of the esters of pyrrolidyl alcohols synthesized by Doyle, Mehta, and Sach (unpublished observations). Of these compounds only the benzilic and diphenylacetic acid esters of 1-methyl-2-hydroxymethylpyrrolidine have previously been reported (Blicke and Lu, 1955). METHODS Tests in VitroAnti-acetylcholine Action. -Segments, approximately 2 cm. long, were removed from the lower ileum of young guinea-pigs weighing not more than 250 g. and suspended in oxygenated Tyrode solution at 370 in a 5 ml. bath. Acetylcholine (ACh), which was allowed to act for 30 sec., was added at 2 min. intervals until constant responses were obtained. The doses of atropine and test compound were added 30 sec. before ACh and were adjusted so that the ACh response was reduced to approximately 30% and 70% of the original. Between the successive doses of antagonist the ACh response was allowed to return to normal. A 16-point assay was then performed using a Latin square design (Fisher and Yates, 1953) and the results analysed by the procedure of Schild (1942). Segments 2 to 3 cm. long, cut from the mid-portion of the jejunum of young rabbits weighing approximately 1.5 kg., were suspended in Tyrode solution at 370. An identical statistical procedure to that used for the guinea-pig ileum anti-ACh assay was employed. A 4 min. cycle was used. The antagonist was added 60 sec. before the ACh. Fresh rabbit jejunum often gave irregular responses to ACh for the first 1 or 2 hr.; regular responses were obtained more rapidly, without loss in sensitivit...

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“…or hydrogen chloride. 2 ) However, ethyl tJ,tJdimethylglycidate. was isomerized to ethyl tJ,tJdimethylpyruvate in very low yield in the presence of sulfuric acid under heating.…”

Section: Figmentioning

confidence: 99%