Studies on the Synthesis of Compounds Related to Adenosine 3', 5'-Cyclic Phosphate. VII. : Synthesis and Cardiac Effects of N^6,N^6-Dialkyl Adenosine 3', 5'-Cyclic Phosphates

スポンサーリンク

概要

• 論文の詳細を見る

• A series of novel N^6,N^6-dialkyl adenosine 3', 5'-cyclic phosphates (N^6,N^6-dialkyl cAMPs) was synthesized from 2'-O-p-toluenesulfonyl cAMP (2'-O-tosyl cAMP, 2) and tested for inotropic and chronotropic activities in vitro.Treatment of 2 with excess alkyl halides and sodium hydride followed by detosylation with aqueous NaOH readily gave N^6,N^6-dialkyl cAMPs (3) in good yields. Various N^6,N^6-dialkyl cAMPs having different alkyl groups at the N^6-position (9-12) were prepared by alkylatin followed by detosylation of N^6-alkyl-2'-O-tosyl cAMPs (4) which were obtained by the reductive alkylation of 2 with aldehydes in the presenve of sodium cyanoborohydride in acetic acid or tosylation of N^6-methyl cAMP. The mechanism of the detosylation is briefly discussed. Among the N^6,N^6-dialkylated derivatives, N^6,N^6-dipentyl (3f) and N^6-ethyl-N^6-heptyl (10e) derivatives were found to exhibit a potent positive inotropic effect and a weak positive chronotropic effect. The structure-activity relationships for the position and the length of alkyl residue are discussed.

• 社団法人日本薬学会の論文
• 1990-11-25

著者

• 加藤 元彦

  Research And Development Division Kikkoman Corporation

• 河田 登美枝

  Department Of Pharmacology School Of Medicine Niigata University

• 片岡 茂博

  Research and Development Division, Kikkoman Corporation

• 山次 信幸

  Research and Development Division, Kikkoman Corporation

• 今井 昭一

  Department of Pharmacology, School of Medicine, Niigata University

• 片岡 茂博

  キッコーマン

• 今井 昭一

  Department Of Pharmacology School Of Medicine Niigata University

• 山次 信幸

  Research And Development Division Kikkoman Corporation

関連論文

• Sytheses of 2-Chloro-4-nitrophenyl β-D-Maltopentaosides with Bulky Modification and Their Application to the Differential Assay of Human α-Amylases
• Studies on the Synthesis of Compounds Related to Adenosine 3', 5'-Cyclic Phosphate. VII. : Synthesis and Cardiac Effects of N^6,N^6-Dialkyl Adenosine 3', 5'-Cyclic Phosphates
• Studies on the Synthesis of Compounds Related to Adenosine-3', 5'-cyclic Phosphate. VI. : Synthesis and Cardiac Effects of N^6,N^6,2'-O-Trialkyl-, N^6,2'-O-Dialkyl-, and 2'-O-Alkyladenosine-3', 5'-cyclic Phosphates
• Studies on the Synthesis of Compounds Related to Adenosine 3', 5'-Cyclic Phosphate. V. : Synthesis and Cardiac Effect of N^6-Alkyladenosine 3', 5'-Cyclic Phosphates and Their 8-Benzylthio Derivatives
• 低カルシウム食で飼育した卵巣摘出ラットの骨密度低下に対するイソフラボンアグリコンを含有する大豆発酵抽出物の予防効果
• P-27 ルミノメーター(ATPフォトメーター)を用いた迅速簡便な細胞増殖抑制率の算出
• Analytical Chemical Studies on Steroids. XX. Zimmermann Reaction and Deuterium Exchange Reactivity of Oxosteroids and Related Compounds
• Glycosides Having Chromophores as Substrates for Sensitive Enzyme Analysis. II. Synthesis of Phenolindophenyl-β-D-glucopyranosides Having an Electron-Withdrawing Substituent as Substrates for β-Glucosidase
• Glycosides Having Chromophores as Substrates for Sensitive Enzyme Analysis. I. : Synthesis of Phenolindophenyl-β-D-glucopyranosides as Substrates for β-Glucosidase
• Inotropic and Chronotropic Actions of 2-Substituted and 8-Substituted Derivatives of Adenosine 3', 5'-Cyclic Monophosphate
• Studies on the Synthesis of Compounds related to Adenosine 3', 5'-Cyclic Phosphate. IV. The Synthesis of 2-Sulfo- and 2-Carboxy-adenosine 3', 5'-Cyclic Phosphate
• Studies on the Synthesis of Compounds related to Adenosine 3', 5'-Cyclic Phosphate. III. The Synthesis of 2-Halogenoadenosine 3', 5'-Cyclic Phosphate
• Studies on the Syntheses of Compounds related to Adenosine 3', 5'-cyclic Phosphate. II. Removal of Etheno Group of 2-Substituted 1,N^6-Etheno-adenosine 3', 5'-cyclic Phosphates
• The Synthesis of 2-Substituted 1,N^6-Etheno-adenosine-3', 5'-cyclic Phosphate by Ring Reclosure of Alkali-hydrolizate of 1,N^6-Etheno-adenosine-3', 5'-cyclic Phosphate
• Chemical Modifications of Androsta-1,4-diene-3,17-dione. III. The Synthesis of (20R)-17α, 20,21-Trihydroxypregna-1,4-dien-3-one and Its Derivatives
• Stereochemistry of Δ^ Unsaturation in Microbial Transformation of Cholesterol
• Synthesis of 1,2- and 2,3-Dimethoxy-4-methylestratrienes
• The Synthesis and Zimmermann Reaction of Some Androsten-16-ones
• Analytical Chemical Studies on Steroids. VII. The Zimmermann Complexes Derived from i-Androstanolone and Its Related 17-Oxosteroids
• Analytical Chemical Studies on Steroids. IV. The Zimmermann Reaction of 16- and 17-Oxosteroids
• Synthesis of 4-Aminophenyl N-Acetyl-β-D-glucosaminide Derivatives and Their Application to the Rate-Assay of N-Acetyl-β-D-glucosaminidase
• Glycosides Having Chromophores as Substrates for Sensitive Enzyme Analysis. V. Synthesis of 6'-O-Substituted 2'-7'-Dichlorofluorescein N-Acetyl-β-D-glucosaminides as Substrates for the Rate-Assay of N-Acetyl-β-D-glucosaminidase
• Glycosides Having Chromophores as Substrates for Sensitive Enzyme Analysis. IV. Synthesis of N-Acetyl-β-D-glucosaminides of Fluorescein Derivatives and Their Application to the Rate-Assay of N-Acetyl-β-D-glucosaminidase
• Studies on the Synthesis of COmpounds Related to Adenosine 3', 5'-Cyclic Phosphate. IX. Synthesis and Cytotoxic Effect of Adenosine 3', 5'-Cyclic Alkylphosphoramidates
• 赤ワインの有効成分プロアントシアニジン : なぜ赤ワインが体に良いのか
• 醸造物の機能性 醤油香気成分の抗腫瘍効果
• NOVEL SELECTIVE INHIBITOR OF α-AMYLASE ISOENZYMES
• THE ACTION OF THIAMINE TETRAHYDROFURFURYL DISULFIDE ON DOG HEART-LUNG PREPARATION
• 本醸造醤油の機能性(醸造食品の機能性)
• 香りの意外性 : 醤油香気成分の発ガン抑制効果(バイオミディア2000)
• CARDIAC ACTION OF DIMORPHOLAMINE
• A STUDY ON THE STRUCTURE-ACTIVITY RELATIONSHIP OF THE CARDIOTONIC STEROIDS

もっと見る 閉じる

スポンサーリンク