N-phenyl-α-D-ribopyranosylamine | 79549-86-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-phenyl-α-D-ribopyranosylamine
• 英文别名: N-Phenyl-α-D-ribopyranosylamin；D-Ribose-phenylimin；(2S,3R,4R,5R)-2-anilinooxane-3,4,5-triol
• CAS: 79549-86-3
• 化学式: C₁₁H₁₅NO₄
• 分子量: 225.244
• InChiKey: KDWDKNMYEVXZLV-DBIOUOCHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  82
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-phenyl-α-D-ribopyranosylamine 在 1,4-二氧六环 作用下， 65.0~75.0 ℃ 、3.43 MPa 条件下， 生成 N-Ribityl-anilin
  参考文献：
  名称：

  ARYLAMINE - N - GLYCOSIDES. PART II. ARYLAMINE - N - PENTOSIDES AND COMPLEX SALT FORMATION STUDIES

  摘要：

  DOI：

  10.1021/jo01171a012
• 作为产物：
  描述：

  N-(2,3,4-tri-O-acetyl-α,β-D-ribopyranosyl)aniline 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 1.5h， 以85%的产率得到N-phenyl-α-D-ribopyranosylamine
  参考文献：
  名称：

  溶液中d-核糖胺的NMR研究：伯胺的衍生物

  摘要：

  摘要Nmr光谱（1 H，13 C）已显示伯胺与d-核糖缩合，主要生成d-核糖吡喃糖基胺，其中1 C 4构象的α端基异构体占优势。β端基异构体主要呈现4 C 1构象。因此，有可能推论N-苯基-d-核糖胺的结构并使某些文献数据相关。对于2，3-O-异亚丙基-d-呋喃呋喃糖基胺衍生物，异亚丙基甲基的13 Cn.mr信号的Δδ值可用于建立异头构型。

  DOI：

  10.1016/0008-6215(83)88214-7

文献信息

• The infrared spectra of N-substituted glycosylamines
  作者：G. P. Ellis

  DOI：10.1039/j29660000572

  日期：——

  The infrared spectra of a number of N-substituted glycosylamines have been examined over the ranges 1800–1500 and 960–700 cm.–1; the spectra indicate the presence of a pyranose ring. Comparison of the spectra of the two isomeric N-phenyl-D-ribosylamines with those of methyl β-D-ribopyranoside and methyl and benzyl β-D-ribofuranoside, suggests that the ribosylamines are pyranose but a furanose structure

  在1800-1500厘米和960-700厘米范围内检查了许多N取代的糖胺的红外光谱。–1 ; 光谱表明存在吡喃糖环。比较两种异构的N-苯基-D-核糖胺与甲基β- D-核糖吡喃糖苷和甲基和苄基β- D-核糖呋喃糖苷的光谱，表明核糖胺是吡喃糖，但在此不能完全排除呋喃糖结构，因为光谱中存在的大量峰的一半。没有光谱学证据表明较早的暗示，某些糖基胺具有无环结构。描述了许多新的糖胺。
• Evaluation of a human monocytic cell line THP-1 model for assay of the intracellular activities of antimicrobial agents against Legionella pneumophila
  作者：H. Takemura、H. Yamamoto、H. Kunishima、H. Ikejima、T. Hara、K. Kanemitsu、S. Terakubo、Y. Shoji、M. Kaku、J. Shimada

  DOI：10.1093/jac/46.4.589

  日期：2000.10.1

  We examined the intracellular activities of 11 antimicrobial agents against Legionella pneumophila using a human monocyte-derived cell line, THP-1. Colony counting and microscopic examination of L. pneumophila co-incubated with THP-1 cells (5 × 105 cells/well) were performed. Both extra- and intra-cellular multiplication of L. pneumophila were observed and were dependent on the inoculum of L. pneumophila in the culture; L. pneumophila did not grow in the cell culture medium alone. Light microscopic examination confirmed that extracellular L. pneumophila originated from THP-1 cells disrupted by bacterial multiplication. L. pneumophila multiplied by 3–4 logs after 24 h incubation with THP-1 cells and their number remained stable at 106–107 cfu/mL until 72 h. The results of viability studies using four antimicrobial agents—ciprofloxacin, erythromycin, minocycline and rifampicin—demonstrated that our system was suitable for the intracellular activity assay. We used a concept of ‘minimum extracellular concentration inhibiting intracellular multiplication’ (MIEC) to evaluate the intracellular activity of antimicrobial agents. The MIECs of three β-lactams were markedly higher than their conventional MICs while those of macrolides, quinolones, rifampicin and minocycline were similar to their MICs. Our results suggest that evaluation of the clinical efficacy of drugs against L. pneumophila should include determination of their intracellular activity against the bacteria, which could be measured using our assay system in THP-1 cells.

  我们利用人体单核细胞衍生细胞系 THP-1 研究了 11 种抗菌剂对嗜肺军团菌的细胞内活性。我们对与 THP-1 细胞（5 × 105 个细胞/孔）共培养的嗜肺军团菌进行了菌落计数和显微镜检查。观察到嗜肺叶球菌在细胞外和细胞内繁殖，这取决于培养基中的嗜肺叶球菌接种量；嗜肺叶球菌不会单独在细胞培养基中生长。光学显微镜检查证实，细胞外的嗜肺叶球菌来自被细菌繁殖破坏的 THP-1 细胞。使用四种抗菌剂--环丙沙星、红霉素、米诺环素和利福平进行的存活率研究结果表明，我们的系统适用于细胞内活性检测。我们使用 "抑制细胞内繁殖的最小细胞外浓度"（MIEC）的概念来评估抗菌剂的细胞内活性。三种β-内酰胺类药物的 MIECs 明显高于其常规 MICs，而大环内酯类、喹诺酮类、利福平和米诺环素的 MIECs 与其 MICs 相近。我们的研究结果表明，在评估抗嗜肺病毒药物的临床疗效时，应包括测定这些药物对该细菌的细胞内活性。
• Acceptability of Prophylactic Mastectomy in Cancer-Prone Women
  作者：F. Eisinger

  DOI：10.1001/jama.283.2.202

  日期：2000.1.12
• Tsuiki, Tohoku Journal of Experimental Medicine, 1955, vol. 61, p. 365,377
  作者：Tsuiki

  DOI：——

  日期：——
• N.m.r. studies of d-ribosylamines in solution: Derivatives of primary amines
  作者：Claude Chavis、Chantal de Gourcy、Françoise Dumont、Jean-Louis Imbach

  DOI：10.1016/0008-6215(83)88214-7

  日期：1983.2

  the 1 C 4 conformation preponderates; the β anomer assumes mainly the 4 C 1 conformation. Thus, it is possible to deduce the structures of the N -phenyl- d -ribosylamines and to correlate some of the literature data. For 2,3- O -isopropylidene- d -ribofuranosylamine derivatives, the Δδ values for the 13 C-n.m.r. signals of the isopropylidene methyl groups can be used to establish the anomeric configuration

  摘要Nmr光谱（1 H，13 C）已显示伯胺与d-核糖缩合，主要生成d-核糖吡喃糖基胺，其中1 C 4构象的α端基异构体占优势。β端基异构体主要呈现4 C 1构象。因此，有可能推论N-苯基-d-核糖胺的结构并使某些文献数据相关。对于2，3-O-异亚丙基-d-呋喃呋喃糖基胺衍生物，异亚丙基甲基的13 Cn.mr信号的Δδ值可用于建立异头构型。