(2S,3S,4R)-N"-cyano-N-(6-nitro-3,4-dihydro-3-hydroxy-2-methyl-2-dimethoxymethyl-2H-benzopyran-4-yl)-N'-(4-methoxybenzyl)guanidine | 335381-78-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (2S,3S,4R)-N"-cyano-N-(6-nitro-3,4-dihydro-3-hydroxy-2-methyl-2-dimethoxymethyl-2H-benzopyran-4-yl)-N'-(4-methoxybenzyl)guanidine
• 英文别名: 1-cyano-3-[(2S,3S,4R)-2-(dimethoxymethyl)-3-hydroxy-2-methyl-6-nitro-3,4-dihydrochromen-4-yl]-2-[(4-methoxyphenyl)methyl]guanidine
• CAS: 335381-78-7
• 化学式: C₂₃H₂₇N₅O₇
• 分子量: 485.497
• InChiKey: GPEKLIXUDCWZMJ-QTEQDKRBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  35
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  163
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (2S,3S,4R)-N"-cyano-N-(6-nitro-3,4-dihydro-3-hydroxy-2-methyl-2-dimethoxymethyl-2H-benzopyran-4-yl)-N'-(4-methoxybenzyl)guanidine 在 sodium tetrahydroborate 、 copper diacetate 作用下， 以 甲醇 、 水 为溶剂， 反应 1.0h， 生成 (2S,3S,4R)-N"-cyano-N-(6-amino-3,4-dihydro-3-hydroxy-2-methyl-2-dimethoxymethyl-2H-benzopyran-4-yl)-N'-(4-methoxybenzyl)guanidine
  参考文献：
  名称：

  A Novel Anti-Ischemic ATP-Sensitive Potassium Channel (K_ATP) Opener without Vasorelaxation:  N-(6-Aminobenzopyranyl)-N‘-benzyl-N‘ ‘-cyanoguanidine Analogue

  摘要：

  This paper describes the design, synthesis, and biological evaluation of a novel anti-ischemic compound, (2S,3S,4R)-N-(6-amino-3,4-dihydro-2-dimethoxymethyl-3-hydroxy-2-methyl-2H-benzopyranyl)-N'-benzyl-N " -cyanoguanidine (33), and the structure-activity relationships leading to the discovery of this compound. Compound 33 significantly reduced the myocardial infarct zone to area at risk (IZ/AAR) in the ischemic myocardium rat model with high cardioselectivity. Since the cardioprotective effect of compound 33 is reversed by ATP-sensitive potassium channel (K-ATP) blockers, its anti-ischemic effect appears to be at least mediated by K-ATP opening. In addition, compound 33 shows good protective activity on neuronal cells against oxidative stress, and therefore it is suggested that compound 33 may have therapeutic potential both in cardio- and in neuroprotection.

  DOI：

  10.1021/jm010183f
• 作为产物：
  描述：

  (2S)-2-dimethoxymethyl-2-methyl-6-nitro-2H-1-benzopyran 在 ammonium hydroxide 、 sodium hypochlorite 、 disodium hydrogenphosphate 、 (S,S)-Mn(III)-salen 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 生成 (2S,3S,4R)-N"-cyano-N-(6-nitro-3,4-dihydro-3-hydroxy-2-methyl-2-dimethoxymethyl-2H-benzopyran-4-yl)-N'-(4-methoxybenzyl)guanidine
  参考文献：
  名称：

  A Novel Anti-Ischemic ATP-Sensitive Potassium Channel (K_ATP) Opener without Vasorelaxation:  N-(6-Aminobenzopyranyl)-N‘-benzyl-N‘ ‘-cyanoguanidine Analogue

  摘要：

  This paper describes the design, synthesis, and biological evaluation of a novel anti-ischemic compound, (2S,3S,4R)-N-(6-amino-3,4-dihydro-2-dimethoxymethyl-3-hydroxy-2-methyl-2H-benzopyranyl)-N'-benzyl-N " -cyanoguanidine (33), and the structure-activity relationships leading to the discovery of this compound. Compound 33 significantly reduced the myocardial infarct zone to area at risk (IZ/AAR) in the ischemic myocardium rat model with high cardioselectivity. Since the cardioprotective effect of compound 33 is reversed by ATP-sensitive potassium channel (K-ATP) blockers, its anti-ischemic effect appears to be at least mediated by K-ATP opening. In addition, compound 33 shows good protective activity on neuronal cells against oxidative stress, and therefore it is suggested that compound 33 may have therapeutic potential both in cardio- and in neuroprotection.

  DOI：

  10.1021/jm010183f

文献信息

• Topical Formulations Comprising Ion Channel Modulators
  申请人：Blum Steven

  公开号：US20110020453A1

  公开（公告）日：2011-01-27

  Disclosed herein are pharmaceutical formulations comprising particles of formula 1: wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , n and * are each defined in specification. Also disclosed are methods of decreasing intraocular pressure comprising topically applying a benzopyranyl guanidine derivative of formula 1 to an eye.
• TOPICAL OPHTHALMIC PHARMACEUTICAL FORMULATION OF (2S,3S,4R)-N''-CYANO-N-(6-AMINO-3,4-DIHYDRO-3-HYDROXY-2-METHYL-2-DIMETHOXYMETHYL-2H-BENZOPYRAN-4-YL)-N'-BENZYLGUANIDINE
  申请人：Blum Steven

  公开号：US20110070310A1

  公开（公告）日：2011-03-24

  A topical ophthalmic pharmaceutical formulation may include particles of the compound (2S,3S,4R)—N″-cyano-N-(6-amino-3,4-dihydro-3-hydroxy-2-methyl-2-dimethoxymethyl-2H-benzopyran-4-yl)-N′-benzylguanidine suspended in a solution comprising monobasic sodium phosphate monohydrate, disodium phosphate heptahydrate, edetate disodium, benzalkonium chloride, sodium chloride, polysorbate 80, and water. A method of treating glaucoma may include topically applying to the eye of a patient in need thereof a therapeutically effective amount of this formulation.
• US6323238B1
  申请人：——

  公开号：US6323238B1

  公开（公告）日：2001-11-27
• [EN] TOPICAL FORMULATIONS COMPRISING ION CHANNEL MODULATORS<br/>[FR] FORMULATIONS TOPIQUES COMPRENANT DES MODULATEURS DE CANAUX IONIQUES
  申请人：MESH THERAPEUTICS LLC

  公开号：WO2010091362A2

  公开（公告）日：2010-08-12

  Disclosed herein are pharmaceutical formulations comprising particles of formula (1) : wherein R1, R2, R3, R4, R5, R6, n and * are each defined in specification. Also disclosed are methods of decreasing intraocular pressure comprising topically applying a benzopyranyl guanidine derivative of formula 1 to an eye.