(1R,2S,3R,5R)-3-氨基-5-(羟甲基)环戊烷-1,2-二醇 | 85026-59-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: (1R,2S,3R,5R)-3-氨基-5-(羟甲基)环戊烷-1,2-二醇
• 英文名称: (-)-(1R,2R,3S,4R)-4-amino-2,3-dihydroxy-1-(hydroxymethyl)cyclopentane
• 英文别名: (-)-(amino-cis-4-dihydroxy-trans-2,3-hydroxymethyl)-1 cyclopentane；(1R,2S,3R,5R)-3-amino-5-(hydroxymethyl)cyclopentane-1,2-diol；(1R,2S,3R,5R)-3-amino-5-hydroxymethylcyclopentane-1,2-diol；(4a-carba-β-D-ribofuranosyl)amine；(1R,2S,3R,4R)-2,3-dihydroxy-4-(hydroxymethyl)-1-aminocyclopentane；(1R,2S,3R,5R)-3-amino-5-hydroxymethyl-cyclopentane-1,2-diol
• CAS: 85026-59-1
• 化学式: C₆H₁₃NO₃
• 分子量: 147.174
• InChiKey: FHNKBDPGQXLKRW-KAZBKCHUSA-N

物化性质

• 沸点：
  300.9±42.0 °C(Predicted)
• 密度：
  1.352±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  86.7
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1R,2S,3R,5R)-3-氨基-5-(羟甲基)环戊烷-1,2-二醇 在 吡啶 、 磷酸三甲酯 、 sodium acetate 、 对甲苯磺酸 、 formamide 、 manganese(ll) chloride 、 三氯氧磷 作用下， 以 甲醇 为溶剂， 反应 22.0h， 生成 1-((1R,2S,3R,4R)-4-((((((((2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)hydroxyphosphoryl)oxy)oxidophosphoryl)oxy)methyl)-2,3-dihydroxycyclopentyl)-3-carbamoylpyridin-1-ium
  参考文献：
  名称：

  Synthesis of Carba-NAD and the Structures of Its Ternary Complexes with SIRT3 and SIRT5

  摘要：

  Carba-NAD is a synthetic compound identical to NAD except for one substitution, where an oxygen atom adjacent to the anomeric linkage bearing nicotinamide is replaced with a methylene group. Because it is inert in nicotinamide displacement reactions, carba-NAD is an unreactive substrate analogue for NAD-consuming enzymes. SIRT3 and SIRT5 are NAD-consuming enzymes that are potential therapeutic targets for the treatment of metabolic diseases and cancers. We report an improved carba-NAD synthesis, including a pyrophosphate coupling method that proceeds in approximately 60% yield. We also disclose the Xray crystal structures of the ternary complexes of SIRT3 and SIRT5 bound to a peptide substrate and carba-NAD. These X-ray crystal structures provide critical snapshots of the mechanism by which human sirtuins function as protein deacylation catalysts.

  DOI：

  10.1021/jo301067e
• 作为产物：
  描述：

  methyl (+)-cis-4-acetamidocyclopent-2-enecarboxylate 在 盐酸 、 四氧化锇 、 三乙基硼氢化锂 、 N-甲基吗啉氧化物 作用下， 以 水 、 叔丁醇 为溶剂， 反应 4.5h， 生成 (1R,2S,3R,5R)-3-氨基-5-(羟甲基)环戊烷-1,2-二醇
  参考文献：
  名称：

  Synthèse des deux énantiomères de l'analogue carbocyclique du nicotinamide ribose et évaluation de leurs propriétés biologiques

  摘要：

  DOI：

  10.1016/0223-5234(89)90086-x

文献信息

• [EN] BIARYL COMPOUNDS USEFUL AS IMMUNOMODULATORS<br/>[FR] COMPOSÉS BIARYLES UTILES EN TANT QU'IMMUNOMODULATEURS
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2018044963A1

  公开（公告）日：2018-03-08

  The present disclosure generally relates to compounds useful as immunomodulators. Provided herein are compounds, compositions comprising such compounds, and methods of their use. The disclosure further pertains to pharmaceutical compositions comprising at least one compound according to the disclosure that are useful for the treatment of various diseases, including cancer and infectious diseases.

  本公开涉及通常用作免疫调节剂的化合物。本文提供了包含这些化合物的组合物，以及它们的使用方法。该公开进一步涉及包含至少一种根据本公开的化合物的药物组合物，用于治疗各种疾病，包括癌症和传染病。
• Substituted pyridine and pyrimidine derivatives and their use in treating viral infections
  申请人：Arasappan Ashok

  公开号：US09433621B2

  公开（公告）日：2016-09-06

  The present invention provides compounds of Formula (I): and tautomers, isomers, and esters of said compounds, and pharmaceutically acceptable salts, solvates, and prodrugs of said compounds, wherein each of R, R1, X, Y, Z, R2, R3, R4, R5, R6, R7, R8, R9, R18, R19 and n is selected independently and as defined herein. Compositions comprising such compounds are also provided. The compounds of the invention are effective as inhibitors of HCV, and are useful, alone and together with other therapeutic agents, in treating or preventing diseases or disorders such as viral infections and virus-related disorders.

  本发明提供了式(I)的化合物：以及所述化合物的互变异构体、异构体和酯，以及所述化合物的药学上可接受的盐、溶剂化合物和前药，其中R、R1、X、Y、Z、R2、R3、R4、R5、R6、R7、R8、R9、R18、R19和n中的每个都是独立选择并如本文所定义。还提供了包含这些化合物的组合物。本发明的化合物作为HCV的抑制剂是有效的，并且在治疗或预防病毒感染和与病毒相关的疾病或紊乱方面，单独或与其他治疗剂一起使用是有用的。
• [EN] SUBSTITUTED PYRIDINE AND PYRIMIDINE DERIVATIVES AND THEIR USE IN TREATING VIRAL INFECTIONS<br/>[FR] DÉRIVÉS DE PYRIDINE ET PYRIMIDINE SUBSTITUÉES ET LEUR UTILISATION DANS LE TRAITEMENT D'INFECTIONS VIRALES
  申请人：SCHERING CORP

  公开号：WO2010022121A1

  公开（公告）日：2010-02-25

  The present invention provides compounds of Formula (I): and tautomers, isomers, and esters of said compounds, and pharmaceutically acceptable salts, solvates, and prodrugs of said compounds, wherein wherein each of R, R1, X, Y, Z, R2, R3, R4, R5, R6, R7, R8, R9, R18, R19 and n is selected independently and as defined herein. Compositions comprising such compounds are also provided. The compounds of the invention are effective as inhibitors of HCV, and are useful, alone and together with other therapeutic agents, in treating or preventing diseases or disorders such as viral infections and virus-related disorders.

  本发明提供了式(I)的化合物：以及所述化合物的互变异构体、同分异构体和酯，以及所述化合物的药学上可接受的盐、溶剂化合物和前药，其中R、R1、X、Y、Z、R2、R3、R4、R5、R6、R7、R8、R9、R18、R19和n中的每个均独立选择并如本文所定义。还提供了包含这些化合物的组合物。本发明的化合物作为HCV的抑制剂是有效的，并且在治疗或预防病毒感染和与病毒相关的疾病或紊乱方面，单独或与其他治疗剂一起使用是有用的。
• Heteroaryl compounds useful as inhibitors of E1 activating enzymes
  申请人：Claiborne F. Christopher

  公开号：US20080051404A1

  公开（公告）日：2008-02-28

  This invention relates to compounds that inhibit E1 activating enzymes, pharmaceutical compositions comprising the compounds, and methods of using the compounds. The compounds are useful for treating disorders, particularly cell proliferation disorders, including cancers, inflammatory and neurodegenerative disorders; and inflammation associated with infection and cachexia.

  这项发明涉及抑制E1激活酶的化合物，包括这些化合物的药物组合物，以及使用这些化合物的方法。这些化合物可用于治疗疾病，特别是细胞增殖性疾病，包括癌症、炎症和神经退行性疾病；以及与感染和虚弱相关的炎症。
• METHOD AND SUBSTANCES FOR PREPARATION OF N-SUBSTITUTED PYRIDINIUM COMPOUNDS
  申请人：Gebauer Peter

  公开号：US20130303768A1

  公开（公告）日：2013-11-14

  A method for the synthesis of N-substituted 3-acylated pyridinium compounds by reacting a pentamethine precursor with a primary amine.

  一种通过将五甲基前体物与一级胺反应合成N-取代3-酰基吡啶化合物的方法。