(2R,3R)-2,3-dihydroxybutanedioic acid 4-(4-{3-[(3R)-3-(dimethylamino)pyrrolidin-1-yl]propoxy}phenyl)benzonitrile hydrate

• ChemBase编号: 154235
• 分子式: C26H35N3O8
• 平均质量: 517.5714
• 单一同位素质量: 517.2424151
• SMILES: CN(C)[C@@H]1CCN(C1)CCCOc1ccc(cc1)c1ccc(cc1)C#N.[C@@H]([C@H](C(=O)O)O)(C(=O)O)O.O
• Canonical SMILES: OC(=O)[C@@H]([C@H](C(=O)O)O)O.N#Cc1ccc(cc1)c1ccc(cc1)OCCCN1CC[C@H](C1)N(C)C.O
• InChI: InChI=1S/C22H27N3O.C4H6O6.H2O/c1-24(2)21-12-14-25(17-21)13-3-15-26-22-10-8-20(9-11-22)19-6-4-18(16-23)5-7-19;5-1(3(7)8)2(6)4(9)10;/h4-11,21H,3,12-15,17H2,1-2H3;1-2,5-6H,(H,7,8)(H,9,10);1H2/t21-;1-,2-;/m11./s1
• InChIKey: BWZMVOINNVPOGW-LZXZYUBDSA-N

名称和登记号

名称

• IUPAC标准名: (2R,3R)-2,3-dihydroxybutanedioic acid 4-(4-{3-[(3R)-3-(dimethylamino)pyrrolidin-1-yl]propoxy}phenyl)benzonitrile hydrate
• IUPAC传统名: 4-(4-{3-[(3R)-3-(dimethylamino)pyrrolidin-1-yl]propoxy}phenyl)benzonitrile L(+)-tartaric acid hydrate
• 别名: 4′-[3-[3(R)-Dimethylamino-1-pyrrolidinyl]propoxy]-[1,1-biphenyl]-4′-carbonitrile L-tartrate hydrate; A-331440 L-tartrate hydrate

登记号

• CAS号: 392338-13-5(freebase)
• PubChem SID: 162248374
• PubChem CID: 71311819

理论计算性质

• 质子受体: 4
• 质子供体: 0
• LogD (pH = 5.5): -0.31751436
• LogD (pH = 7.4): 1.0834454
• Log P: 3.3643467
• 摩尔折射率: 106.8492 cm^3
• 极化性: 42.76552 Å^3
• 极化表面积: 39.5 Å^2
• 可自由旋转的化学键: 10
• 里宾斯基五规则: false

分子性质

理化性质

• 溶解度: DMSO: ≥10 mg/mL; ethanol: insoluble; H2O: insoluble; methanol: insoluble
• 外观: white to off-white solid

安全信息

• 德国WGK号: 3
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

产品相关信息

• 纯度: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C22H27N3O · xC4H6O6 · yH2O

详细说明

Sigma Aldrich - A3104

Legal Information
Subject to U.S. Patent numbers 6,515,013 and 6,620,839. Sold under license from Abbott Laboratories
Biochem/physiol Actions
Histamine affects homeostatic mechanisms, including food and water consumption, by acting on central nervous system (CNS) receptors. Presynaptic histamine H3 receptors regulate release of histamine and other neurotransmitters, and histamine H3 receptor antagonists enhance neurotransmitter release. A-331440 [4′-[3-(3(R)-(dimethylamino)-pyrrolidin-1-yl)-propoxy]-biphenyl-4-carbonitrile] is a histamine H3 receptor antagonist which binds potently and selectively to both human and rat histamine H3 receptors (Ki<=25 nM). Mice were stabilized on a high-fat diet (45 kcal % lard) prior to 28-day oral b.i.d. dosing for measurement of obesity-related parameters. A-331440 administered at 0.5 mg/kg had no significant effect on weight, whereas 5 mg/kg decreased weight comparably to dexfenfluramine (10 mg/kg). A-331440 administered at 15 mg/kg reduced weight to a level comparable to mice on the low-fat diet. The two higher doses reduced body fat and the highest dose also normalized an insulin tolerance test. These data show that the histamine H3 receptor antagonist, A-331440, has potential as an antiobesity agent.