3-羟基苯硫醇钠 | 71681-94-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: 3-羟基苯硫醇钠
• 英文名称: sodium 3-hydroxybenzenethiolate
• CAS: 71681-94-2
• 化学式: C₆H₅OS*Na
• 分子量: 148.161
• InChiKey: WFIHKXPBMIKSOU-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  9.0
• 可旋转键数：
  0.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2-溴代异丁酸甲酯 、 3-羟基苯硫醇钠 以 乙腈 为溶剂， 以81%的产率得到methyl 2-(3-hydroxyphenylthio)isobutyrate
  参考文献：
  名称：

  [EN] USE OF alpha-PHENYLTHIOCARBOXYLIC AND alpha-PHENYLOXYCARBOXYLIC ACIDS WITH SERUM-GLUCOSE-LOWERING AND SERUM-LIPID-LOWERING ACTIVITY
  [FR] UTILISATION D'ACIDES 20040708WO03059875A2SIGMA TAU IND FARMACEUTI [IT], et al200307241,74-7,14,17,18,20-26PX1-7,10,15PXWINEGAR D A ET AL: "Role of peroxisome proliferator-activated receptors in atherosclerosis", CURRENT OPINION IN CARDIOVASCULAR, PULMONARY AND RENAL INVESTIGATIONAL DRUGS 2000 UNITED KINGDOM, vol. 2, no. 3, 2000, pages 233 - 243, XP008029337, ISSN: 1464-8482WINEGAR D A ET ALRole of peroxisome proliferator-activated receptors in atherosclerosisCURRENT OPINION IN CARDIOVASCULAR, PULMONARY AND RENAL INVESTIGATIONAL DRUGS 2000 UNITED KINGDOM2000231464-8482233243page 236, left-hand column, last paragraph237L1,21X1,2,7,8,10-12,15XBROOKS D A ET AL: "Design and synthesis of 2-methyl-2-{4-[2-(5-methyl-2- aryloxazol-4-yl)ethoxy]phenoxy}propionic acids: a new class of dual PPARalpha/gamma agonists", JOURNAL OF MEDICINAL CHEMISTRY, AMERICAN CHEMICAL SOCIETY. WASHINGTON, US, vol. 44, no. 13, 21 June 2001 (2001-06-21), pages 2061 - 2064, XP002184099, ISSN: 0022-2623BROOKS D A ET ALDesign and synthesis of 2-methyl-2-{4-[2-(5-methyl-2- aryloxazol-4-yl)ethoxy]phenoxy}propionic acids: a new class of dual PPARalpha/gamma agonistsJOURNAL OF MEDICINAL CHEMISTRY, AMERICAN CHEMICAL SOCIETY. WASHINGTON, US2001062144130022-262320612064Chart 112063R1,2X1-3,7,10-12,15XLALEZARI I ET AL: "LR-16 A COMPOUND WITH POTENT EFFECTS ON THE OXYGEN AFFINITY OF HEMOGLOBIN ON BLOOD CHOLESTEROL AND ON LOW DENSITY LIPOPROTEIN", PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES, vol. 85, no. 16, 1988, 1988, pages 6117 - 6121, XP001161155, ISSN: 0027-8424LALEZARI I ET ALLR-16 A COMPOUND WITH POTENT EFFECTS ON THE OXYGEN AFFINITY OF HEMOGLOBIN ON BLOOD CHOLESTEROL AND ON LOW DENSITY LIPOPROTEINPROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES1988198885160027-842461176121Scheme 1page 6117, abstractX1,2,10-12,15XUS3262850AMOSS JONES WILLIAM GLYNNE, et al19660726111719X1,2,10-12,15XGB1422679AFUNAI PHARMACEUTICAL IND LTD19760128112126X1,2,7,10-12,15XGRONOWITZ S ET AL: "POTENTIAL HYPOLIPIDEMIC AGENTS XIX. SYNTHESIS AND LIPID-LOWERING PROPERTIES OF THIOPHENE DERIVATIVES RELATED TO CLOFIBRATE", ACTA PHARMACEUTICA SUECICA, XX, XX, vol. 15, no. 5, 1978, pages 361 - 367, XP001053343, ISSN: 0001-6675GRONOWITZ S ET ALPOTENTIAL HYPOLIPIDEMIC AGENTS XIX. SYNTHESIS AND LIPID-LOWERING PROPERTIES OF THIOPHENE DERIVATIVES RELATED TO CLOFIBRATEACTA PHARMACEUTICA SUECICA, XX, XX19781550001-667536136713641X1,3,10-12,15XDURIEZ P ET AL: "POST-STATIN APPROACHES TO HYPERLIPIDAEMIA", EXPERT OPINION ON INVESTIGATIONAL DRUGS, ASHLEY PUBLICATIONS LTD., LONDON, GB, vol. 7, no. 12, December 1998 (1998-12-01), pages 1997 - 2009, XP000892408, ISSN: 1354-3784DURIEZ P ET ALPOST-STATIN APPROACHES TO HYPERLIPIDAEMIAEXPERT OPINION ON INVESTIGATIONAL DRUGS, ASHLEY PUBLICATIONS LTD., LONDON, GB1998127121354-37841997200920023.1Y1-15YBROWN P J ET AL: "A Ureido-Thiobutyric Acid (GW9578) is a subtype-Selective PPARalpha Agonist with Potent lipid-Lowering Activity", JOURNAL OF MEDICINAL CHEMISTRY, AMERICAN CHEMICAL SOCIETY. WASHINGTON, US, vol. 42, no. 19, 9 April 1999 (1999-04-09), pages 3785 - 3788, XP002128791, ISSN: 0022-2623BROWN P J ET ALA Ureido-Thiobutyric Acid (GW9578) is a subtype-Selective PPARalpha Agonist with Potent lipid-Lowering ActivityJOURNAL OF MEDICINAL CHEMISTRY, AMERICAN CHEMICAL SOCIETY. WASHINGTON, US1999040942190022-262337853788Chart 1page 3787, left-hand column, last paragraphY1-15YGUERRE-MILLO MICHELE ET AL: "Peroxisome proliferator-activated receptor alpha activators improve insulin sensitivity and reduce adiposity", JOURNAL OF BIOLOGICAL CHEMISTRY, vol. 275, no. 22, 2 June 2000 (2000-06-02), pages 16638 - 16642, XP002275720, ISSN: 0021-9258GUERRE-MILLO MICHELE ET ALPeroxisome proliferator-activated receptor alpha activators improve insulin sensitivity and reduce adiposityJOURNAL OF BIOLOGICAL CHEMISTRY20000602275220021-9258166381664216641R3Y1-15YZHANG BEI B ET AL: "New approaches in the treatment of type 2 diabetes", CURRENT OPINION IN CHEMICAL BIOLOGY, vol. 4, no. 4, August 2000 (2000-08-01), pages 461 - 467, XP002275721, ISSN: 1367-5931ZHANG BEI B ET ALNew approaches in the treatment of type 2 diabetesCURRENT OPINION IN CHEMICAL BIOLOGY200008441367-5931461467463L31Y1-15YHAWKE ROY L ET AL: "Potent hypocholesterolemic activity of novel ureido phenoxyisobutyrates correlates with their intrinsic fibrate potency and not with their ACAT inhibitory activity", JOURNAL OF LIPID RESEARCH, vol. 38, no. 6, 1997, pages 1189 - 1203, XP002275722, ISSN: 0022-2275HAWKE ROY L ET ALPotent hypocholesterolemic activity of novel ureido phenoxyisobutyrates correlates with their intrinsic fibrate potency and not with their ACAT inhibitory activityJOURNAL OF LIPID RESEARCH19973860022-227511891203entire documentAA

  摘要：

  本文描述了使用具有以下公式（I）的α-苯基硫代羧酸和α-苯基氧羧酸的衍生物进行制备药物，用于预防和治疗糖尿病，特别是2型糖尿病、其并发症、各种形式的胰岛素抵抗和高脂血症。其中，取代基的含义在文本中有描述。

  公开号：

  WO2004056355A1
• 作为产物：
  描述：

  3-羟基苯硫酚 在 sodium hydride 作用下， 以 乙腈 为溶剂， 反应 0.08h， 生成 3-羟基苯硫醇钠
  参考文献：
  名称：

  [EN] USE OF alpha-PHENYLTHIOCARBOXYLIC AND alpha-PHENYLOXYCARBOXYLIC ACIDS WITH SERUM-GLUCOSE-LOWERING AND SERUM-LIPID-LOWERING ACTIVITY
  [FR] UTILISATION D'ACIDES 20040708WO03059875A2SIGMA TAU IND FARMACEUTI [IT], et al200307241,74-7,14,17,18,20-26PX1-7,10,15PXWINEGAR D A ET AL: "Role of peroxisome proliferator-activated receptors in atherosclerosis", CURRENT OPINION IN CARDIOVASCULAR, PULMONARY AND RENAL INVESTIGATIONAL DRUGS 2000 UNITED KINGDOM, vol. 2, no. 3, 2000, pages 233 - 243, XP008029337, ISSN: 1464-8482WINEGAR D A ET ALRole of peroxisome proliferator-activated receptors in atherosclerosisCURRENT OPINION IN CARDIOVASCULAR, PULMONARY AND RENAL INVESTIGATIONAL DRUGS 2000 UNITED KINGDOM2000231464-8482233243page 236, left-hand column, last paragraph237L1,21X1,2,7,8,10-12,15XBROOKS D A ET AL: "Design and synthesis of 2-methyl-2-{4-[2-(5-methyl-2- aryloxazol-4-yl)ethoxy]phenoxy}propionic acids: a new class of dual PPARalpha/gamma agonists", JOURNAL OF MEDICINAL CHEMISTRY, AMERICAN CHEMICAL SOCIETY. WASHINGTON, US, vol. 44, no. 13, 21 June 2001 (2001-06-21), pages 2061 - 2064, XP002184099, ISSN: 0022-2623BROOKS D A ET ALDesign and synthesis of 2-methyl-2-{4-[2-(5-methyl-2- aryloxazol-4-yl)ethoxy]phenoxy}propionic acids: a new class of dual PPARalpha/gamma agonistsJOURNAL OF MEDICINAL CHEMISTRY, AMERICAN CHEMICAL SOCIETY. WASHINGTON, US2001062144130022-262320612064Chart 112063R1,2X1-3,7,10-12,15XLALEZARI I ET AL: "LR-16 A COMPOUND WITH POTENT EFFECTS ON THE OXYGEN AFFINITY OF HEMOGLOBIN ON BLOOD CHOLESTEROL AND ON LOW DENSITY LIPOPROTEIN", PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES, vol. 85, no. 16, 1988, 1988, pages 6117 - 6121, XP001161155, ISSN: 0027-8424LALEZARI I ET ALLR-16 A COMPOUND WITH POTENT EFFECTS ON THE OXYGEN AFFINITY OF HEMOGLOBIN ON BLOOD CHOLESTEROL AND ON LOW DENSITY LIPOPROTEINPROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES1988198885160027-842461176121Scheme 1page 6117, abstractX1,2,10-12,15XUS3262850AMOSS JONES WILLIAM GLYNNE, et al19660726111719X1,2,10-12,15XGB1422679AFUNAI PHARMACEUTICAL IND LTD19760128112126X1,2,7,10-12,15XGRONOWITZ S ET AL: "POTENTIAL HYPOLIPIDEMIC AGENTS XIX. SYNTHESIS AND LIPID-LOWERING PROPERTIES OF THIOPHENE DERIVATIVES RELATED TO CLOFIBRATE", ACTA PHARMACEUTICA SUECICA, XX, XX, vol. 15, no. 5, 1978, pages 361 - 367, XP001053343, ISSN: 0001-6675GRONOWITZ S ET ALPOTENTIAL HYPOLIPIDEMIC AGENTS XIX. SYNTHESIS AND LIPID-LOWERING PROPERTIES OF THIOPHENE DERIVATIVES RELATED TO CLOFIBRATEACTA PHARMACEUTICA SUECICA, XX, XX19781550001-667536136713641X1,3,10-12,15XDURIEZ P ET AL: "POST-STATIN APPROACHES TO HYPERLIPIDAEMIA", EXPERT OPINION ON INVESTIGATIONAL DRUGS, ASHLEY PUBLICATIONS LTD., LONDON, GB, vol. 7, no. 12, December 1998 (1998-12-01), pages 1997 - 2009, XP000892408, ISSN: 1354-3784DURIEZ P ET ALPOST-STATIN APPROACHES TO HYPERLIPIDAEMIAEXPERT OPINION ON INVESTIGATIONAL DRUGS, ASHLEY PUBLICATIONS LTD., LONDON, GB1998127121354-37841997200920023.1Y1-15YBROWN P J ET AL: "A Ureido-Thiobutyric Acid (GW9578) is a subtype-Selective PPARalpha Agonist with Potent lipid-Lowering Activity", JOURNAL OF MEDICINAL CHEMISTRY, AMERICAN CHEMICAL SOCIETY. WASHINGTON, US, vol. 42, no. 19, 9 April 1999 (1999-04-09), pages 3785 - 3788, XP002128791, ISSN: 0022-2623BROWN P J ET ALA Ureido-Thiobutyric Acid (GW9578) is a subtype-Selective PPARalpha Agonist with Potent lipid-Lowering ActivityJOURNAL OF MEDICINAL CHEMISTRY, AMERICAN CHEMICAL SOCIETY. WASHINGTON, US1999040942190022-262337853788Chart 1page 3787, left-hand column, last paragraphY1-15YGUERRE-MILLO MICHELE ET AL: "Peroxisome proliferator-activated receptor alpha activators improve insulin sensitivity and reduce adiposity", JOURNAL OF BIOLOGICAL CHEMISTRY, vol. 275, no. 22, 2 June 2000 (2000-06-02), pages 16638 - 16642, XP002275720, ISSN: 0021-9258GUERRE-MILLO MICHELE ET ALPeroxisome proliferator-activated receptor alpha activators improve insulin sensitivity and reduce adiposityJOURNAL OF BIOLOGICAL CHEMISTRY20000602275220021-9258166381664216641R3Y1-15YZHANG BEI B ET AL: "New approaches in the treatment of type 2 diabetes", CURRENT OPINION IN CHEMICAL BIOLOGY, vol. 4, no. 4, August 2000 (2000-08-01), pages 461 - 467, XP002275721, ISSN: 1367-5931ZHANG BEI B ET ALNew approaches in the treatment of type 2 diabetesCURRENT OPINION IN CHEMICAL BIOLOGY200008441367-5931461467463L31Y1-15YHAWKE ROY L ET AL: "Potent hypocholesterolemic activity of novel ureido phenoxyisobutyrates correlates with their intrinsic fibrate potency and not with their ACAT inhibitory activity", JOURNAL OF LIPID RESEARCH, vol. 38, no. 6, 1997, pages 1189 - 1203, XP002275722, ISSN: 0022-2275HAWKE ROY L ET ALPotent hypocholesterolemic activity of novel ureido phenoxyisobutyrates correlates with their intrinsic fibrate potency and not with their ACAT inhibitory activityJOURNAL OF LIPID RESEARCH19973860022-227511891203entire documentAA

  摘要：

  本文描述了使用具有以下公式（I）的α-苯基硫代羧酸和α-苯基氧羧酸的衍生物进行制备药物，用于预防和治疗糖尿病，特别是2型糖尿病、其并发症、各种形式的胰岛素抵抗和高脂血症。其中，取代基的含义在文本中有描述。

  公开号：

  WO2004056355A1

文献信息

• The introduction of P4 substituted 1-methylcyclohexyl groups into Boceprevir®: A change in direction in the search for a second generation HCV NS3 protease inhibitor
  作者：Frank Bennett、Yuhua Huang、Siska Hendrata、Raymond Lovey、Stephane L. Bogen、Weidong Pan、Zhuyan Guo、Andrew Prongay、Kevin X. Chen、Ashok Arasappan、Srikanth Venkatraman、Francisco Velazquez、Latha Nair、Mousumi Sannigrahi、Xiao Tong、John Pichardo、Kuo-Chi Cheng、Viyyoor M. Girijavallabhan、Anil K. Saksena、F. George Njoroge

  DOI：10.1016/j.bmcl.2010.02.063

  日期：2010.4

  In the search for a second generation HCV protease inhibitor, molecular modeling studies of the X-ray crystal structure of Boceprevir (R) 1 bound to the NS3 protein suggest that expansion into the S4 pocket could provide additional hydrophobic Van der Waals interactions. Effective replacement of the P4 tertbutyl with a cyclohexylmethyl ligand led to inhibitor 2 with improved enzyme and replicon activities. Subsequent modeling and SAR studies led to the pyridine 38 and sulfone analogues 52 and 53 with vastly improved PK parameters in monkeys, forming a new foundation for further exploration. (C) 2010 Elsevier Ltd. All rights reserved.