6,6'-bis-O-(2-tetradecylhexadecanoyl)-α,α'-trehalose | 99697-30-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 糖脂
• 英文名称: 6,6'-bis-O-(2-tetradecylhexadecanoyl)-α,α'-trehalose
• 英文别名: [(2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(2-tetradecylhexadecanoyloxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl 2-tetradecylhexadecanoate
• CAS: 99697-30-0
• 化学式: C₇₂H₁₃₈O₁₃
• 分子量: 1211.88
• InChiKey: ZSICNRPFEXKZRF-DIJREYLGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  25.4
• 重原子数：
  85
• 可旋转键数：
  62
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  202
• 氢给体数：
  6
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  在 palladium hydroxide, 20 wt% on carbon 、 氢气 作用下， 以 甲醇 、 氯仿 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 8.0h， 以96%的产率得到6,6'-bis-O-(2-tetradecylhexadecanoyl)-α,α'-trehalose
  参考文献：
  名称：

  Development of Vizantin, a Safe Immunostimulant, Based on the Structure–Activity Relationship of Trehalose-6,6′-dicorynomycolate

  摘要：

  Vizantin, 6,6'-bis-O-(3-nonyldodecanoy1)-alpha,alpha'-trehalose, was developed as a safe immunostimulator on the basis of a structure-activity relationship (SAR) study with trehalose 6,6'-dicorynomycolate (TDCM). It was possible to synthesize vizantin on a large scale more easily than in the case of TDCM, and the compound exhibited more potent prophylactic effect on experimental lung metastasis of B16-F0 melanoma cells. Because vizantin stimulated human macrophages, it is a promising candidate for clinical application.

  DOI：

  10.1021/jm3016443

文献信息

• Lethal and adjuvant activities of cord factor (trehalose-6,6'-dimycolate) and synthetic analogs in mice.
  作者：FUMIO NUMATA、KEIKO NISHIMURA、HIDEHARU ISHIDA、SHIGEKI UKEI、YUKIKO TONE、CHIAKI ISHIHARA、IKUO SAIKI、ISAO SEKIKAWA、ICHIRO AZUMA

  DOI：10.1248/cpb.33.4544

  日期：——

  Mycobacterial glycolipid, trehalose-6, 6'-dimycolate (TDM), and its analogs, 6, 6'-di-O-triacontanoyl-α, α-trehalose [TD (L30)], 6, 6'-bis-O-(2-tetradecylhexadecanoyl)-α, α-trehalose [TD-(B30)], 6, 6'-bis-O-(3-hydroxy-2-tetradecyloctadecanoyl)-α, α-trehalose [TD (BH32)], 6, 6'-bis-O-(2-docosyl-3-hydroxyhexacosanoyl)-α, α-trehalose [TD (BH48)], 6, 6'-bis-O-(3-tetradecanoyloxy-tetradecanoyl)-α, α-trehalose [TD (D28)], 6, 6'-dideoxy-6, 6'-bis (mycoloylamino)-α, α-trehalose [TDNM] and 6, 6'-dideoxy-6, 6'-bis (3-hydroxy-2-tetradecyloctadecanoylamino)-α, α-trehalose [TDN (BH32)], were synthesized, and their lethal and adjuvant activities were examined. TDM and TDNM were lethal when injected intravenously into mice at a dose of 150 μg as 9% oil-in-water emulsion, but the other analogs showed no lethal toxicity to mice at the same dose. The cytolytic activity of mouse peritoneal macrophages against tumor cells was potentiated by intraperitoneal injection of TDM and its synthetic analogs. TDM and TD (BH32) also stimulated nonspecific host resistance against Sendai virus infection in BALB/c mice.

  分枝杆菌糖脂，曲哈洛糖-6，6'-二甲氧基酸酯（TDM）及其类似物，6，6'-二-O-三碳酰基-α，α-曲哈洛糖[TD (L30)]，6，6'-双-O-(2-十四烷基十六烷酰基)-α、6，6'-双-O-(3-羟基-2-十四烷基十八烷酰基)-α，α-三卤糖[TD-(B30)]，6，6'-双-O-(2-二十二烷基-3-羟基二十六烷酰基)-α、6，6'-双-O-(2-二十二烷基-3-羟基二十六烷酰)-α，α-三卤糖[TD (BH48)]，6，6'-双-O-(3-十四烷酰氧基-十四烷酰)-α，α-三卤糖[TD (D28)]，6，6'-双脱氧-6，6'-双(霉菌酰氨基)-α，α-三卤糖[TDNM]和 6、合成了 6, 6'-dideoxy-6, 6'-bis (3-hydroxy-2-tetradecyloctadecanoylamino)-α, α-trehalose[TDN（BH32）]，并检测了它们的致死活性和佐剂活性。当小鼠静脉注射剂量为 150 μg 的 9% 水包油型乳剂时，TDM 和 TDNM 具有致死性，但在相同剂量下，其他类似物对小鼠无致死毒性。腹腔注射 TDM 及其合成类似物可增强小鼠腹腔巨噬细胞对肿瘤细胞的细胞溶解活性。TDM 和 TD (BH32) 还能激发 BALB/c 小鼠对仙台病毒感染的非特异性宿主抵抗力。
• Development of Vizantin, a Safe Immunostimulant, Based on the Structure–Activity Relationship of Trehalose-6,6′-dicorynomycolate
  作者：Hirofumi Yamamoto、Masataka Oda、Mayo Nakano、Naoyuki Watanabe、Kenta Yabiku、Masahiro Shibutani、Masahisa Inoue、Hiroshi Imagawa、Masahiro Nagahama、Seiichiro Himeno、Kojun Setsu、Jun Sakurai、Mugio Nishizawa

  DOI：10.1021/jm3016443

  日期：2013.1.10

  Vizantin, 6,6'-bis-O-(3-nonyldodecanoy1)-alpha,alpha'-trehalose, was developed as a safe immunostimulator on the basis of a structure-activity relationship (SAR) study with trehalose 6,6'-dicorynomycolate (TDCM). It was possible to synthesize vizantin on a large scale more easily than in the case of TDCM, and the compound exhibited more potent prophylactic effect on experimental lung metastasis of B16-F0 melanoma cells. Because vizantin stimulated human macrophages, it is a promising candidate for clinical application.