Synthesis and Analgesic Activity of Novel Heterocycles, [1]Benzothiopyrano[3,4-b]pyrrole Derivatives

スポンサーリンク

概要

• 論文の詳細を見る

• In order to develop analgesic compounds possessing a sulfur atom in the alicyclic ring, novel cis-fused heterocycles, [1]benzothiopyrano[3,4-b]pyrrole derivatives (II) were synthesized via a unique cyclization reaction starting from 4-(4-methoxyphenylthio)-2-butanone (1) or 6-methoxy-3,4-dihydro-2H-1-benzothiopyran-4-one (7).The analgesic effects of benzothiopyranopyrroles (16,18) were measured by means of the writhing test. The phenolic derivative 18 completely inhibited the appearance of writhing at the dose of 50 mg/kg, but the methoxy derivative 16 had no analgesic effect.

• 社団法人日本薬学会の論文
• 1989-05-25

著者

• 清水 洋

  岐阜薬科大学

• 木戸 勝

  Laboratories Of Natural Product Chemistry Tokushima Research Institute Otsuka Pharmaceutical Co. Ltd

• 岩田 憲之

  Nagoya Laboratory Sanwa Kagaku Kenkyusho Ltd.

• 清水 洋

  Gifu Pharmaceutical University

• 堀 幹夫

  Gifu Pharmaceutical University

• 今井 英治

  Gifu Pharmaceutical University

• 黒野 昌庸

  Nagoya Laboratory, Sanwa Kagaku Kenkyusho, Ltd.,

• 河村 典広

  Gifu Pharmaceutical University

• 黒野 昌庸

  Nagoya Laboratory Sanwa Kagaku Kenkyusho Ltd.

• 片山 貞

  Gifu Pharmaceutical University

• 中野 万正

  Nagoya Laboratory, Sanwa Kagaku Kenkyuusho Ltd.,

• 中野 万正

  Nagoya Laboratory Sanwa Kagaku Kenkyuusho Ltd.

関連論文

• チオピリリウム塩および関連硫黄化合物の極性付加環化反応の開発と新規ヘテロ環構築への応用
• Generation of Selenabenzenes Bearing an Electron-Withdrawing Group at the 2-Position
• Generation and Alkylation of α-Lithio-Se, O-heteroacetals, and Stereoselective Cyclization of Olefinic Se, O-Heteroacetals
• Reactions of 9-Phenylthioxanthene 10-Oxide with Organometallic Reagents
• Synthesis and Reactions of 10-Chloro-10,9-(epoxyalkano)selenoxanthenes and 1-Chloro-1-phenyl-3H-2,1-benzoxaselenoles
• 2-Methylisoselenochromanium Salts : Spectroscopic Properties and Reactions
• Synthesis of 2,6-Epithio-3-benzazocine Derivatives
• Facile Synthesis of 8-Benzoylthio-2,6-methano-3-benzazocines and 3-Benzoylthiomorphinans Having Small-Ring Substituents
• Synthesis and Analgetic Activity of Sulfur-Containing Morphinans and Related Compounds
• Synthesis and Reactions of 1-Thianaphthalenes
• Synthesis and thermal Reactions of Cyano-Stabilized Cyclic Sulfur Ylides, 2-Alkyl-1-cyano-3,4-dihydro-1H-2-thionianaphthalen-1-ides
• チアベンゼンと関連環状硫黄イリド類--合成とその多様な反応性
• Ring Contraction of 2-Chlorocyclohexanone with Grignard Reagents
• Generation and Properties of N^7-Xanthinium Ylides : Reactions of N^7-Xanthinium Ylides with Diphenylcyclopropenone and Acetylenic Compounds
• Reactions of 8,9-Dihydroxanthines with Acetylenic Compounds. Formation of Heteropropellanes
• 10-Alkyl-9-arylthioxathenium Salt類の合成と立体化学
• 1,4-イリド性Thiaanthracenesの新規転位反応
• Synthesis and Analgesic Activity of Novel Heterocycles, [1]Benzothiopyrano[3,4-b]pyrrole Derivatives
• Synthesis of Some N-Substituted 1,2,3,4,5,6-Hexahydro-2,6-methano-3-benzazocines (6,7-Benzomorphans)
• 5,7-Ethano-4,5,5a, 6,7,1lb-hexa-hydro-2,6,7-trimethyl-1H-benzo[g]homoquinolin-9-01 and 4,6-Ethano-3,4,4a, 5,6,10b-hexahydro-2,5,6-trimethylbenzo[f]quinolin-8-olのアゴニスト-アンタゴニスト性
• 5,7-Ethano-4,5,5a, 6,7,1lb-hexahydro-2,6,7-trimethyl-1H-benzo[g]homoquinolin-9-olと4,6-Ethano-3,4,4a, 5,6,10b-hexahydro-2,5,6-trimethylbenzo[f]quinolin-8-olの合成
• AGONIST-ANTAGONIST PROPERTIES OF 5,7-ETHANO-4,5,5a, 6,7,11b-HEXAHYDRO-2,6,7-TRIMETHYL-1H-BENZO [g] HOMOQUINOLIN-9-OL AND 4,6-ETHANO-3,4,4a, 5,6,10b-HEXAHYDRO-2,5,6-TRIMETHYLBENZO [f] QUINOLIN-8-OL
• Sulfur-Containing Acylamino Acids. II. Syntheses and Angiotensin I Converting Enzyme-Inhibitory Activities of N-Mercaptoal-kanoyl-S-ethyl-L-cysteine(Medicinal Chemistry,Chemical)
• Sulfur-Containing Acylamino Acids. I. Syntheses and Angiotensin I Converting Enzyme-Inhibitory Activities of Sulfur-Containing N-Mercaptoalkanoyl Amino Acids(Medicinal Chemistry,Chemical)
• On the Diterpenoids of Andrographis paniculata : X-Ray Crystallographic Analysis of Andrographolide and Structure Determination of New Minor Diterpenoids
• Studies on Benzothiazoline Derivatives. IV. Synthesis and Novel Ring Expansion Reaction of Benzothiazoline Sulfoxides
• Studies on Benzothiazoline Derivatives. III. Reactions of 2,2-Disubstituted Benzothiazolines with Haloacyl Halides or Acid Anhydrides
• A New Aspect on Alkylation of Benzothiazolines
• Benzothiazoline誘導体に関する研究(第1報)2-Aryl-3-methylbenzothiazoline類の合成とその酸化開環反応
• Photochemistry of 2-(N-Acyl-N-alkylamino)cyclohex-2-enones : Formation of Spiro-β-lactams(Organic,Chemical)
• 新規なHalosulfuranes, 5-Chloro-および5-Bromo-5,11-epoxy-6,11-dihydrodibenzo[b, e]thiepinの合成と構造
• Constituents of Cinnamomi Cortex. V. Structures of Five Novel Diterpenes, Cinncassiols D_1,D_1 Glucoside, D_2,D_2 Glucoside and D_3
• 58 桂皮ジテルペンの化学的研究
• 新規な双環セレヌラン類 : 10-Chloro-10,9-epoxyethanoselenoxanthenes類の合成と性質
• Selenoxanthen-10-io(alkoxalyl alkoxycarbonyl)methanide類および関連化合物の合成, 立体化学ならびに反応
• Synthesis, Stereochemistry and Reactions of Selenoxanthen-10-io (alkoxalyl alkoxycarbonyl) methanides and Related Compounds
• cisおよびtrans-9-Phenylselenoxanthene-N-arylsulfonyl-selenilimine類の化学
• 安定なSelenoxanthenium Ylide類 : Selenoxanthen-10-io(alkoxalyl alkoxycarbonyl)methanide類ならびにその関連化合物の合成と新しい還元的環化反応
• Xanthinium N(7)-Ylide類とトランスオレフンィン型Dipolarophile類の付加環化反応
• 新規なキサンチニウムイリド類の環変換反応
• Xanthine誘導体の新規な環変換反応
• 新環状硫黄イリド類, 8-Thiaazulenesと求電子試薬の反応
• 麻薬性鎮痛薬, ベンゾモルファン誘導体 その構造活性相関に関する展望
• パラコート, ジクワット及びその関連化合物に関する還元生成物のガスクロマトグラフィー : N-アルキルピリジニウム化合物のNaBH_4-NiCl_2系還元法におけるピリジン環の還元的環開裂反応とその抑制について
• パラコート, ジクワット及びその関連化合物に関する還元生成物のガスクロマトグラフィー : NaBH_4-NiCl_2系還元法によるN-アルキルピリジニウム化合物の還元的環開裂について
• 1-Cyclohexyl-4-(1,2-diphenylethyl)piperazineの鎮痛活性とOpiate Receptor Binding
• 30 沖縄サンゴ礁生物Clavularia属軟サンゴ2種の成分研究
• Marine Natural Products. XII. On the Chemical Constituents of the Okinawan Marine Sponge Hymeniacidon aldis
• CLAVUKERIN A, A NEW TRINOR-GUAIANE SESQUITERPENE FROM THE OKINAWAN SOFT CORAL CLAVULARIA KOELLIKERI
• THREE NEW ent-VALERENANE SESQUITERPENES FROM AN OKINAWAN SOFT CORAL
• Stichlorogenol and Dehydrostichlorogenol, Genuine Aglycones of Stichlorosides A_1,B_1,C_1 and A_2,B_2,C_2,from the Sea Cucumber Stichopus Chloronotus (BRANDT)
• 新規含硫黄鎮痛薬S-Etorphineの合成
• 麻薬性鎮痛薬(1,2-Diphenylethyl)piperazines : 絶対配置と麻薬受容体親和性における特異な相関性
• 副作用の少ない新規非麻薬性強力鎮痛薬の合成 : 2-Acylthio-ならびに2'-Alkythio-6,7-benzomorphan類
• 2-Alkyl (or Aryl)-1-benzoyl-3,4-dihydro-1H-2-thionianaphthalen-1-ide類と酸性水素をもつ化合物との熱反応
• SYNTHESIS OF THE NOVEL SULFUR-CONTAINING ANALGESIC S-ETORPHINE
• Dibenzothiophenes and Related Compounds. IV. Reactions of 5-Substituted 10,11-Dihydrodibenzo [b, f] thiepinium Salts with Aryllithiums
• 環状硫黄イリド類の熱反応の新様式
• Studies on the Syntheses of Analgesics. VI. Synthesis of 1,2,3,4,5,6-Hexahydro-1,5-methano-3-benzazocine Derivatives
• Studies on the Syntheses of Analgesics. IV. Syntheses of 1,2,3,4-Tetrahydro-5H-benzazepine Derivatives
• Intramolecular [2+2] Photocycloaddition of 2-[N-Acyl-N-(2-propenyl)-amino] cyclohex-2-enones : Synthesis of 2-Azabicyclo [2.1.1] hexanes
• INTRAMOLECULAR PHOTO [2+2] CYCLOADDITION OF 2-ALLYLOXY-AND 2-ALLYLAMINOCYCLOHEX-2-ENONES : FORMATION OF 2-OXA-AND 2-AZA-BICYCLO [2.1.1] HEXANE SYSTEMS
• Synthesis of 2-Aryl-2,3-dihydro-3-piperazinylmethyl-1,5-benzothiazepin-4(5H)-ones and Related Compounds
• 新規強力抗腫瘍薬および胃液分泌抑制薬, (-)-cis-2,3-Dihydro-3-(4-methylpiperazinylmethyl)-2-phenyl-1,5-benzothiazepin-4(5H)-one Hydrochloride(BTM-1086), および関連化合物の合成
• SYNTHESIS OF A NEW POTENT ANTI-ULCER AND GASTRIC SECRETORY INHIBITING AGENT, (-)-cis-2,3-DIHIDRO-3-(4-METHYLPIPERAZINYLMETHYL)-2-PHENYL-1,5-BENZOTHIAZEPIN-4 (5H)-ONE HYDROCHLORIDE (BTM-1086), AND RELATED COMPOUNDS
• 新規環状スルフィルイミン類, 2-Azathiabenzene誘導体の合成と諸性質
• A Novel Ring System, α-Thieno [4,3-f] morphan
• Reactivities of 9-Phenylxanthylium and 9-Phenylthioxanthylium Salts in Electrophilic and Nucleophilic Reactions. I. Nitration
• 10-Thiaanthracenes. I. Mechanism of the Reaction of 3-Phenylthioxanthylium Salt with Organometallic Reagents
• Dibenzothiophenes and Related Compounds. VI. Reactions of Cyclic Sulfonium Salts with Sodium Alkoxides and Benzenethiolate in Alcohols
• Dibenzothiophenes and Related Compounds. V. Reactions of 5-Substituted Dibenzothiophenium Salts with Organometallic Reagents
• Dibenzothiophenes and Related Compounds. III. Reactions of 10-Substituted 9,9-Dimethylthioxanthenium and 5-Substituted Dibenzothiophenium Salts with Organolithiums
• Dibenzothiophenes and Related Compounds. II. Reactions of 5-Substituted Dibenzothiophenium Salts with Organolithiums
• Dibenzothiophene類とその関連化合物に関する研究(第1報)5-Substituted Dibenzothiophenium Salt類ならびに10-Substituted 9,9-Dimethylthioxanthenium Salt類の合成
• 非麻薬性強力鎮痛薬の合成研究
• オクテット
• Studies on the Syntheses of Analgesics. V. Synthesis of 1,2,3,4,5,6-Hexahydro-3-benzazocine Derivatives. (3)
• 9-Arylthioxanthene 10-0xides類および10,10-Dioxide類の立体化学
• Stereochemistry of 9-Arylthioxanthene 10-Oxides and 10,10-Dioxides
• Stable S-Alkylthiabenzenes. Synthesis of 2-Methyl-1-phenyl-2-thianaphthalene
• A New Synthesis of S-Arylthiabenzene Analogues using Grignard Reaction
• チアベンゼンと関連環状硫黄イリド類 : 合成とその多様な反応性
• Dibenzothiepin誘導体およびその関連化合物(第4報)諸種Cyclic Ketone類および6,11-Dihydrodibenzo[b, e]thiepin-11-one 類とSbCl_5の反応
• Dibenzothiepin誘導体およびその関連化合物 (第3報) Triphenylmethyl Hexachloroantimonate の反応性の研究と6,11-Dihydrodibenzo [b, e]-thiepin-11-ylium Hexachloroantimonate類の合成
• Dibenzothiepin誘導体およびその関連化合物(第1報)11-Phenyl-6,11-dihydrodibenzo[b, e]thiepin-11-ylium Salt類の単離とその新規な脱水素環化反応
• Dibenzothiepin Derivatives and Related Compounds. V. Reactions of 6,11-Dihydrodibenzo [b, e] thiepin 5-Oxides with SbCl_5 and Perchloric Acid
• Dibenzothiepin Derivatives and Related Compounds. II. A Novel Cyclization Reaction of 6-Chloro-11-phenyl-6,11-dihydrodibenzo [b, e] thiepins
• 環状スルホニウムイリド類 : 2-Alkyl(or aryl)-1-benzoyl-1H-2-thianaphthalen-2-ium-1-idesおよび2-Alkyl(or aryl)-1-benzoyl-3,4-dihydro-1H-2-thianaphthalen-2-ium-1-idesの合成と熱反応
• Syntheses and Properties of Novel Cyclic Sulfilimines, 2-Azathiabenzene Derivatives
• Benzothiazoline Sulfoxide類の非立体特異的環拡大反応
• 5員複素環状スルホキシド類の非立体特異的環拡大反応
• 7員複素環状スルホキシド類, 2,2-ジ置換 1,4-および1,5-Benzothiazepine Sulfoxide類の環変換反応
• Non-stereospecific Ring Expansion Reactions of Benzothiazoline Sulfoxides
• Syntheses and Cycloaddition Reactions of Thiaazulenocyclone and Thiaazulenocyclone 8,8-Dioxide
• Selenoxanthylium Salts. I. Nitration of 9-Phenylselenoxanthylium Perchlorate
• Selenabenzenes. I. Synthesis of 10-Selenaanthracene Derivatives
• 10-Thiaanthracene類(第3報)1位に塩基性基を有する10-Phenyl-10-thiaanthracene類の合成
• Thiaazulene類に関する研究(第3報)2-Thiaazulenylium Salt類と求核試薬の反応2-Aryl-2-thiaazulene類の合成
• Thiaazulene類に関する研究(第2報)2-Thiaazulenylium Salt類と求電子試薬の反応
• Thiaazulene類に関する研究(第1報)2-Thiaazulenylium Salt類の合成

もっと見る 閉じる

スポンサーリンク