(1R)-1-C-propyl-1,4-dideoxy-1,4-imino-L-arabinitol | 1186214-05-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (1R)-1-C-propyl-1,4-dideoxy-1,4-imino-L-arabinitol
• 英文别名: β-1-C-propyl-1,4-dideoxy-1,4-imino-L-arabinitol；(2S,3S,4S,5R)-2-(hydroxymethyl)pyrrolidine-5-propyl-3,4-diol；(2S,3S,4S,5R)-2-(hydroxymethyl)-5-propylpyrrolidine-3,4-diol
• CAS: 1186214-05-0
• 化学式: C₈H₁₇NO₃
• 分子量: 175.228
• InChiKey: OPIRYPQUASLBFO-KVPKETBZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  72.7
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  benzyl (2S,3S,4S,5R)-3,4-bis(phenylmethoxy)-2-(phenylmethoxymethyl)-5-prop-2-enylpyrrolidine-1-carboxylate 在 盐酸 、 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 、 异丙醇 为溶剂， 反应 18.0h， 以86%的产率得到(1R)-1-C-propyl-1,4-dideoxy-1,4-imino-L-arabinitol
  参考文献：
  名称：

  [EN] COMPOUNDS FOR THEIR USE AS DRUGS FOR THE TREATMENT AND/OR THE PREVENTION OF INFECTION(S) CAUSED BY BIOFILM-FORMING BACTERIA
  [FR] COMPOSÉS À UTILISER EN TANT QUE MÉDICAMENTS POUR LE TRAITEMENT ET/OU LA PRÉVENTION D'UNE OU DE PLUSIEURS INFECTIONS PROVOQUÉES PAR DES BACTÉRIES GÉNÉRATRICES DE BIOFILM

  摘要：

  本发明涉及以下式(I)的化合物，其中：m表示整数，可以等于0、1、2、3、4、5或6，X表示简单键或基团-CHR1，其中R1表示：-氢原子，或-线性或支链，可能被最多3个来自O、S或N的杂原子中断和/或可能被取代的(C1-C12)-烷基，R2、R3和R4分别独立地表示：-氢原子，或-线性或支链(C1-C12)-烷基或(C1-C12)-酰基，R5表示：-氢原子，或-线性或支链，可能被取代的(C1-C13)-烷基，可能被取代和最多被3个来自O、S或N的杂原子中断，R6表示：-氢原子，或-线性或支链，可能被取代和最多被3个来自O、S或N的杂原子中断的(C1-C12)-烷基，用作抗菌药物，用于治疗和/或预防由生物膜形成细菌引起的感染。

  公开号：

  WO2016030434A1

文献信息

• Dihydroxyacetone Phosphate Aldolase Catalyzed Synthesis of Structurally Diverse Polyhydroxylated Pyrrolidine Derivatives and Evaluation of their Glycosidase Inhibitory Properties
  作者：Jordi Calveras、Meritxell Egido-Gabás、Livia Gómez、Josefina Casas、Teodor Parella、Jesús Joglar、Jordi Bujons、Pere Clapés

  DOI：10.1002/chem.200900838

  日期：2009.7.27

  The polyhydroxylated pyrrolidines generated were tested as inhibitors against seven glycosidases. Among them, good inhibitors of α‐L‐fucosidase (IC50=1–20 μM), moderate of α‐L‐rhamnosidase (IC50=7–150 μM), and weak of α‐D‐mannosidase (IC50=80–400 μM) were identified. The apparent inhibition constant values (Ki) were calculated for the most relevant inhibitors and computational docking studies were

  据报道，通过DHAP醛缩酶的催化，醛醇将磷酸二羟基丙酮磷酸酯（DHAP）加成到C-α-取代的N -Cbz-2-氨基醛衍生物上而生成的吡咯烷型亚氨基糖的化学酶法合成。来自大肠杆菌的L-藻糖-1-磷酸醛缩酶（FucA）和L-鼠李糖-1磷酸醛缩酶（RhuA）用作生物催化剂以在亚氨基糖上产生构型多样性。FucA催化剂可很好地耐受C-α处的烷基线性取代（即40-70％转化为醛醇加合物），而除二甲基和苄基取代（20％）外，未观察到具有C-α-烷基支链取代的产物。 。RhuA是用途最广泛的生物催化剂：C-α-烷基直链基团转化为羟醛加成物的转化率最高（60-99％），而C-α-烷基支链基团的转化率中等至良好（50-80％），二甲基和苄基取代基（20％）除外。FucA是最具立体选择性的生物催化剂（90％至100％的抗（3 R，4 R）加合物）。RhuA对（S）-N具有高度立体选择性-Cbz -2-氨基醛（90-100％顺式（即，3
• Compounds for their use as drugs for the treatment and/or the prevention of infection(s) caused by biofilm-forming bacteria
  申请人：CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE

  公开号：US10745395B2

  公开（公告）日：2020-08-18

  The present invention relates to compounds of the following formula (I), wherein: m represents an integer being equal to 0, 1, 2, 3, 4, 5 or 6, X represents a simple bond or a radical —CHR1 wherein R1 represents:—a hydrogen atom, or—a linear or branched, possibly interrupted by up to 3 heteroatoms selected from O, S or N and/or possibly substituted, (C1-C12)-alkyl, R2, R3 and R4 represent independently from each other:—a hydrogen atom, or—a linear or branched (C1-C12-alkyl or (C1-C12)-acyl R5 represents:—a hydrogen atom, or—a linear or branched, possibly substituted, (C1-C13)-alkyi possibly substituted and possibly interrupted by up to 3 heteroatoms selected from O, S or N, R6 represents:—a hydrogen atom, or—a linear or branched possibly substituted (C1-C12)-alkyl, possibly substituted and possibly interrupted by up to 3 heteroatoms selected from O, S or N, for their use as antibacterial drugs for the treatment and/or the prevention of infection(s) caused by biofilm-forming bacteria.

  本发明涉及下式（I）的化合物，其中：m 代表等于 0、1、2、3、4、5 或 6 的整数，X 代表单键或自由基-CHR1，其中 R1 代表：氢原子，或直链或支链的、可能被最多 3 个选自 O、S 或 N 的杂原子间断的和/或可能被取代的 (C1-C12)- 烷基，R2、R3 和 R4 相互独立地代表：氢原子，或直链或支链的 (C1-C12) - 烷基或 (C1-C12)- 芳基 R5 代表：氢原子，或直链或支链的 (C1-C12)- 烷基或 (C1-C12)- 芳基-氢原子，或直链或支链、可能被取代的（C1-C13）烷基，可能被最多 3 个选自 O、S 或 N 的杂原子取代和间断，R6 代表：氢原子，或直链或支链、可能被取代的（C1-C12）烷基，可能被最多 3 个选自 O、S 或 N 的杂原子取代和间断，用作抗菌药物，用于治疗和/或预防由生物膜形成细菌引起的感染。
• COMPOUNDS FOR THEIR USE AS DRUGS FOR THE TREATMENT AND/OR THE PREVENTION OF INFECTION(S) CAUSED BY BIOFILM-FORMING BACTERIA
  申请人：CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE

  公开号：US20180030047A1

  公开（公告）日：2018-02-01

  Disclosed are compounds of the following formula I: wherein: m represents an integer being equal to 0, 1, 2, 3, 4, 5 or 6, X represents a simple bond or a radical —CHR 1 — wherein R 1 represents: a hydrogen atom, or a linear or branched, possibly interrupted by up to 3 heteroatoms selected from O, S or N and/or possibly substituted, (C 1 -C 12 )-alkyl, R 2 , R 3 and R 4 represent independently from each other: a hydrogen atom, or a linear or branched (C 1 -C 12 )-alkyl or (C 1 -C 12 )-acyl R 5 represents: a hydrogen atom, or a linear or branched, possibly substituted, (C 1 -C 13 )-alkyl possibly interrupted by up to 3 heteroatoms selected from O, S or N, R 6 represents: a hydrogen atom, or a linear or branched possibly substituted (C 1 -C 12 )-alkyl, possibly substituted and possibly interrupted by up to 3 heteroatoms selected from O, S or N, for their use as antibacterial drugs.