6-O-tosylcodeine | 22952-79-0

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 吗啡烷
• 英文名称: 6-O-tosylcodeine
• 英文别名: 4,5α-epoxy-3-methoxy-17-methyl-6α-(toluene-4-sulfonyloxy)-morphin-7-ene；4,5α-Epoxy-3-methoxy-17-methyl-6α-(toluol-4-sulfonyloxy)-morphin-7-en；[(4R,4aR,7S,7aR,12bS)-9-methoxy-3-methyl-2,4,4a,7,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-yl] 4-methylbenzenesulfonate
• CAS: 22952-79-0
• 化学式: C₂₅H₂₇NO₅S
• 分子量: 453.559
• InChiKey: XIZHBEXHAHWBOC-ASDQOZNMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.22
• 重原子数：
  32.0
• 可旋转键数：
  4.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  65.07
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  6-O-tosylcodeine 在 lithium aluminium tetrahydride 、 溶剂黄146 作用下， 以 四氢呋喃 、 xylene 为溶剂， 反应 27.0h， 生成 8β-<2-(Dimethylamino)ethyl>-8,14-dihydro-6-desmethoxythebain
  参考文献：
  名称：

  Fleischhacker, Wilhelm; Richter, Bernd, Chemische Berichte, 1980, vol. 113, # 12, p. 3866 - 3880

  摘要：

  DOI：
• 作为产物：
  描述：

  对甲苯磺酰氯 、 可待因 在 吡啶 作用下， 生成 6-O-tosylcodeine
  参考文献：
  名称：

  脱氧可待因

  摘要：

  描述了可待因-对甲苯磺酸酯的生产及其使用氢化铝锂还原为脱氧可待因E的方法。后者在结构上与文献中提到的脱氧可待因蛋白A，C和D不同，并且对应于式E。此外，以不同的方式制备了已知的吗啡-单-对甲苯磺酸酯。-脱氧可待因（DOC）在小鼠中的毒性约为可待因的两倍。抽筋的效果类似于可待因。从这个发现不可能推断出对其他温血动物的影响。B.可待因不再对人类产生惊厥作用。其止痛作用约为可待因的一半。吗啡在小鼠中的功效大约是其30倍。与相同剂量的可待因相比，DOC使呼吸中枢更多地瘫痪。

  DOI：

  10.1002/hlca.19510340106

文献信息

• Opioids and Efflux Transporters. Part 2: P-Glycoprotein Substrate Activity of 3- and 6-Substituted Morphine Analogs
  作者：Christopher W. Cunningham、Susan L. Mercer、Hazem E. Hassan、John R. Traynor、Natalie D. Eddington、Andrew Coop

  DOI：10.1021/jm701457j

  日期：2008.4.1

  Continuing our studies investigating opioids with reduced P-glycoprotein (P-gp) substrate activity, a series of known 3- and 6-hydroxy, -methoxy, and -desoxymorphine analogs was synthesized and analyzed for Pgp substrate activity and opioid binding affinity. 6-Desoxymorphine (7) showed high affinity for opioid receptors and did not induce P-gp-mediated ATP hydrolysis. Additionally, 7 demonstrated morphine-like antinociceptive potency in mice, indicating this compound as an ideal lead to further evaluate the role of P-gp in opioid analgesic tolerance development.
• Δ⁷- and Δ⁸-Desoxycodeine
  作者：Henry Rapoport、Robert M. Bonner

  DOI：10.1021/ja01150a132

  日期：1951.6
• Goto; Yamamoto, Proceedings of the Japan Academy, 1959, vol. 35, p. 472,474
  作者：Goto、Yamamoto

  DOI：——

  日期：——
• Design, Chemical Synthesis, and Biological Evaluation of Thiosaccharide Analogues of Morphine- and Codeine-6-Glucuronide
  作者：James M. MacDougall、Xiao-Dong Zhang、Willma E. Polgar、Taline V. Khroyan、Lawrence Toll、John R. Cashman

  DOI：10.1021/jm049554t

  日期：2004.11.1

  A series of 6-beta-thiosaccharide analogues of morphine-6-glucuronide (M6G) and codeine-6-glucuronide (C6G) were synthesized and evaluated with the objective of preparing an analogue of M6G with improved biological activity. The affinity of the thiosaccharide analogues of M6G and C6G was examined by competitive binding assays at mu, delta, and kappa opioid receptors. The thiosaccharide compounds in the morphine series 5b, 5e, 6a, and 6c showed 1.5-2.4-fold higher affinity for the mu receptor than M6G, but were generally less selective than M6G. The functional activity of the M6G and C6G analogues was examined with the [S-35]GTP-gamma-S assay. Compounds 5b and 5e were determined to be fully mu agonists, whereas compounds 6a and 6c were partial mu agonists. The in vivo antinociceptive activity of compound 5b was evaluated by the tail flick latency test, giving an ED50 of 2.5 mg/kg.
• The SN2' Reaction. III. Structure and SN2' Reactions of the Halocodides
  作者：Gilbert Stork、Frank H. Clarke

  DOI：10.1021/ja01599a026

  日期：1956.9