N-((S)-1-((1S,2R)-1,2-dihydroxyhexadecyl)-2-((1S,2S,3S,4S,5S,6R)-2,3,4,6-tetrahydroxy-5-hydroxymethylcyclohexylamino)ethyl)cerotamide hydrochloride | 1319731-10-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-((S)-1-((1S,2R)-1,2-dihydroxyhexadecyl)-2-((1S,2S,3S,4S,5S,6R)-2,3,4,6-tetrahydroxy-5-hydroxymethylcyclohexylamino)ethyl)cerotamide hydrochloride
• 英文别名: (2S,3S,4R)-2-hexacosanamide-1-((1'S,2'S,3'S,4'S,5'S,6'R)-5-hydroxymethyl-2,'3',4',6'-tetrahydroxycyclohexylamine)octadecane-3,4-diol hydrochloride；N-[(2S,3S,4R)-3,4-dihydroxy-1-[[(1S,2S,3S,4S,5S,6R)-2,3,4,6-tetrahydroxy-5-(hydroxymethyl)cyclohexyl]amino]octadecan-2-yl]hexacosanamide;hydrochloride
• CAS: 1319731-10-6
• 化学式: C₅₁H₁₀₂N₂O₈*ClH
• 分子量: 907.84
• InChiKey: DXBSIJYHNRDCEZ-TWHNZPQRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.11
• 重原子数：
  62
• 可旋转键数：
  44
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.98
• 拓扑面积：
  183
• 氢给体数：
  10
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  (1R,2S,3S,4S,5S,6S)-2-azido-6-(benzyloxymethyl)-3,4,5-(tribenzyloxy)cyclohexan-1-ol 在 盐酸 、 lithium aluminium tetrahydride 、 5%-palladium/activated carbon 、 氢气 、 caesium carbonate 、 苯硫酚 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 水 、 乙腈 为溶剂， 25.0 ℃ 、202.66 kPa 条件下， 反应 90.0h， 生成 N-((S)-1-((1S,2R)-1,2-dihydroxyhexadecyl)-2-((1S,2S,3S,4S,5S,6R)-2,3,4,6-tetrahydroxy-5-hydroxymethylcyclohexylamino)ethyl)cerotamide hydrochloride
  参考文献：
  名称：

  Galacto-Configured Aminocyclitol Phytoceramides Are Potent in Vivo Invariant Natural Killer T Cell Stimulators

  摘要：

  A new class of a-galactosylceramide (alpha GC) nonglycosidic analogues bearing galacto-configured aminocyclitols as sugar surrogates have been obtained. The aminocyclohexane having a hydroxyl substitution pattern similar to an a-galactoside is efficiently obtained by a sequence involving Evans aldol reaction and ring-closing metathesis with a Grubbs catalyst to give a key intermediate cyclohexene, which has been converted in galacto-aminocyclohexanes that are linked through a secondary amine to a phytoceramide lipid having a cerotyl N-acyl group. Natural Killer T (NKT) cellular assays have resulted in the identification of an active compound, HS161, which has been found to promote NKT cell expansion in vitro in a similar fashion but more weakly than alpha GC. This compound stimulates the release of Interferon-gamma (IFN gamma) and Interleukin-4 (IL-4) in iNKT cell culture but with lower potency than alpha GC. The activation of Invariant Natural Killer T (iNKT) cells by this compound has been confirmed in flow cytometry experiments. Remarkably, when tested in mice, HS161 selectively induces a very strong production of IFN-gamma indicative of a potent Th1 cytokine profile. Overall, these data confirm the agonist activity of alpha GC lipid analogues having charged amino-substituted polar heads and their capacity to modulate the response arising from iNKT cell activation in vivo.

  DOI：

  10.1021/ja202610x

文献信息

• AMINOCYCLITOL COMPOUNDS, PROCESS FOR OBTAINING THEM AND USES
  申请人：Llebaria Soldevilla Amadeo

  公开号：US20120093875A1

  公开（公告）日：2012-04-19

  Aminocyclitol compounds and uses thereof as pharmaceutical compositions for the treatment of diseases associated with alterations in iNKT cells, more specifically autoimmune diseases, cancer, infections caused by pathogenic microorganisms or inflammatory diseases. Furthermore, the invention relates to the process for obtaining said compounds.

  氨基环糖醇化合物及其用途作为制药组合物治疗与iNKT细胞变化相关的疾病，更具体地包括自身免疫性疾病、癌症、由致病微生物引起的感染或炎症性疾病。此外，本发明还涉及获得该化合物的过程。
• EP2409966
  申请人：——

  公开号：——

  公开（公告）日：——