A Novel Histamine 2(H_2) Receptor Antagonist with Gastroprotective Activity. II. Synthesis and Pharmacological Evaluation of 2-Furfuryl-thio and 2-Furfurylsulfinyl Acetamide Derivatives with Heteroaromatic Rings

スポンサーリンク

概要

• 論文の詳細を見る

• We recently found that N-[3-[3-(piperidinomethyl)phenoxy]propyl]acetamide derivatives with a thioether function showed gastric anti-secretory and gastroprotective activities and that the thioether function (particularly furfurylthio or furfurylsulfinyl) was essential for gastroprotection. In the present study, a series of 2-furfurylthio and 2-furfurylsulfinyl acetamide derivatives were synthesized and evaluated for histamine H_2 receptor antagonistic activity, gastric anti-secretory activity and gastroprotective action. Based on the structure of N-[3-[3-(piperidinomethyl)phenoxy]propyl]acetamide, we designed compounds, in which the 3-(piperidinomethyl)phenoxy part is substituted with many types of heteroaromatic ring attached to the tertiary amine and the propyl group is replaced with other carbon linkages. Structure-activity relatioship are discussed. 2-Furfurylsulfinyl-N-[4-[4-(piperidinomethyl)-2-pyridyloxy]-(Z)-2-butenyl]acetamide was the most potent among the tested compounds and was given the code designation FRG-8813.

• 公益社団法人日本薬学会の論文
• 1998-04-15

著者

• Sekine Akihiro

  Pharmaceuticals Research Laboratories Fujirebio Inc.

• Sekine Akihiro

  Department Of Pharmacology Faculty Of Pharmaceutical Sciences Osaka University

• Sekine Akihiro

  東邦大学 薬

• Sekine Y

  Pharmaceuticals Research Laboratories Fujirebio Inc.

• Sekine Yasuo

  Pharmaceuticals Research Laboratories Fujirebio Inc.

• HIRAKAWA Nobuhiko

  Pharmaceuticals Research Laboratories, Fujirebio Inc.

• MATSUMOTO Hajime

  Pharmaceuticals Research Laboratories, Fujirebio Inc.

• HOSODA Akihiko

  Pharmaceuticals Research Laboratories, Fujirebio Inc.

• YAMAURA Tetsuaki

  Pharmaceuticals Research Laboratories, Fujirebio Inc.

• Hosoda A

  Pharmaceuticals Research Laboratories Fujirebio Inc.

• Yamaura Tetsuaki

  Pharmaceuticals Research Laboratories Fujirebio Inc.

• Matsumoto H

  Yamanouchi Pharmaceutical Co. Ltd. Ibaraki Jpn

• Sekine A

  Pharmaceuticals Research Laboratories Fujirebio Inc.

• Yamaura T

  Pharmaceuticals Research Laboratories Fujirebio Inc.

• Hosoda Akihiko

  Pharmaceuticals Research Laboratories Fujirebio Inc.

• Hirakawa Nobuhiko

  Pharmaceuticals Research Laboratories Fujirebio Inc.

関連論文

• The Pummerer Reaction of 2-Vinylcyclopropyl Sulfoxides : Generation and Reaction of Butadienylthionium Ion Intermediates.
• Synthesis and Reactions of Lactam Sulfonium Salts with a Sulfonio Bridgehead. II. 1,1a, 4,5,6-Pentahydro-6-oxo-2H-thiopyrano[1,6-d]-4,1-benzothiazepinium Perchlorates.
• Synthesis and Reactions of Lactam Sulfonium Salts with a Sulfonio Bridgehead. I. 1,4,4a-Trihydro-5-oxo-2H-thiopyrano[1,6-a]-1,4-benzothiazinium Perchlorates.
• Synthesis and Reactions of Lactam Sulfonium Salts with a Sulfonio Bridgehead. II. 1,1a, 4,5,6-Pentahydro-6-oxo-2H-thiopyrano[1,6-d]-4,1-benzothiazepinium Perchlorates
• Amino Acids and Peptides. XXXIX. Synthesis of iNoc-Gln-Val-Val-Ala-Ala-pNA and Its Action on Thiol Proteinases
• THE ACTIONS OF SODIUM NITROPRUSSIDE AND DILTIAZEM ON CALCIUM-, POTASSIUM- AND HISTAMINE-INDUCED CONTRACTILE RESPONSES IN ISOLATED RABBIT BASILAR ARTERY, AORTA, TAENIA COLI AND TRACHEAL SMOOTH MUSCLE
• Antiulcer Effect of Lafutidine on Indomethacin-Induced Gastric Antral Ulcers in Refed Rats
• Syntheses and Thermal Behaviour of 9-Substiuted 9-Thia-10-azaphenanthrenes.
• A Novel Histamine 2(H_2) Receptor Antagonist with Gastroprotective Activity. II. Synthesis and Pharmacological Evaluation of 2-Furfuryl-thio and 2-Furfurylsulfinyl Acetamide Derivatives with Heteroaromatic Rings
• A Novel Histamine 2(H_2) Receptor Antagonist with Gastroprotective Activity. I. Synthesis and Pharmacological Evaluation of N-Phenoxypropylacetamide Derivatives with Thioether Function
• Photochemical[3+2]Cycloaddition of 2'-Vinyl-2H-1,4-benzothiazine-3(4H)-one-2-spirocyclopropanes Catalyzed by Diphenyl Dichalcogenides.
• Conformational Effects on Photochemical Thiylation of 2'-Vinyl-2H-benzothiazine-2-spirocyclopropan-3(4H)-ones.
• Chemical Behavior of 2'-Vinyl-2H-benzothiazine-2-spirocyclopropan-3(4H)-ones in Acidic Media.
• Acid-promoted Isomerisation of 1-Acceptor-1-sulfenyl-substituted 2-Vinylcyclopropanes with C_1-C_2 Bond Fission and Novel 1,5-Sulfenyl rearrangement.
• Photochemical [3+2] Cycloaddition of 2'-Vinyl-2H-1,4-benzothiazin-3(4H)-one-2-spirocyclopropanes Catalyzed by Diphenyl Dichalcogenides
• Conformational Effects on Photochemical Thiylation of 2'-Vinyl-2H-benzothiazine-2-spirocyclopropan-3(4H)-ones
• Chemical Behavior of 2'-Vinyl-2H-benzothiazine-2-spirocyclopropan-3(4H)-ones in Acidic Media
• Acid-promoted C_1-C_2 Bond Fission and Subsequent 1,5-Sulfeny Shift of 1-Acceptor-1-sulfenyl-substituted 2-Vinylcyclopropanes. : Formation of 6-Sulfenyl-α, β-γ, δ-unsaturated Carboxylic Esters and Nitriles
• Generation and Reactions of Butadienylthionium Ions from 2-Vinylcyclopropyl Sulfoxides under Pummerer Conditions
• New Transformation of Lactam Sulfides to Tetrahydro-3,6-epithiobenzazocines via Bicyclic Sulfonium Salts with a Sulfonio Bridgehead.
• Capsaicin-Induced Calcitonin Gene-Related Peptide Release from Isolated Rat Stomach Measured with a New Chemiluminescent Enzyme Immunoassay
• Gastroprotective Activity of FRG-8813, a Novel Histamine H_2-Receptor Antagonist, in Rats
• Effects of F-1394, an Acyl-CoA:Cholesterol Acyltransferase (ACAT) Inhibitor, on ACAT Activity in HepG2 Cells and on Hepatic Secretion of Lipids in Triton WR-1339-Induced Hyperlipidemic Rats: Possible Role of Hepatic ACAT in Very Low Density Lipoprotein Se
• Hypocholesterolemic Action and Prevention of Cholesterol Absorption via the Gut by F-1394, a Potent Acyl-CoA: Cholesterol Acyltransferase (ACAT) Inhibitor, in Cholesterol Diet-Fed Rats
• Studies on Acyl-CoA: Cholesterol Acyltransferase (ACAT) Inhibitory Effects and Enzyme Selectivity of F-1394, a Pantotheic Acid Derivative
• 10-Thia-anthracenes. Part 3. : A Re-examination of the Reaction of 9-Phenylthioxanthylium Salt and Phenyl-lithium.
• Acid-promoted C_1-C_2 Bond Fission and Subsequent 1,5-Sulfenyl Shift of 1-Acceptor-1-sulfenyl-substituted 2-Vinylcyclopropanes. Formation of 6-Sulfenyl-α,β-γ,δ-unsaturated Carboxylic Esters and Nitriles
• A BIOCHEMICAL APPROACH TO THE IMMEDIATE ALLERGIC PHENOMENA AND ITS APPLICATION FOR CREATING NOVEL ANTIALLERGIC AGENTS
• STUDIES ON METHODOLOGY OF FINDING THE ANTI-ALLERGIC AGENT WITH THE GUIDANCE OF ANTI-HYALURONIDASE ACTIVITY
• Thermal Rearrangement of 9-Benzyl-10-aza-9-thiaphenanthrenes.
• Synthesis of Medium-sized Cyclic Sulfides and Selenides by Crosspiece C-X Bond Cleavage of Bicyclic Onium Salts bearing a Bridgehead Sulfur or Selenium Atom.
• Effects of diadenosine tetraphosphate on systemic and regional hemodynamics in dogs

もっと見る 閉じる

スポンサーリンク