1,3,4-tri-O-acetyl-2,6-dideoxy-2-fluoro-5-C-(trifluoromethyl)-α-L-talopyranose | 172939-16-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1,3,4-tri-O-acetyl-2,6-dideoxy-2-fluoro-5-C-(trifluoromethyl)-α-L-talopyranose
• 英文别名: 1,3,4-tri-O-acetyl-2,6-dideoxy-2,6,6,6-tetrafluoro-α-L-talopyranose；[(2S,3R,4R,5S,6R)-2,5-diacetyloxy-3-fluoro-6-(trifluoromethyl)oxan-4-yl] acetate
• CAS: 172939-16-1
• 化学式: C₁₂H₁₄F₄O₇
• 分子量: 346.233
• InChiKey: XRTWCKRGXVRDEM-ZKKRXERASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  88.1
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  1,3,4-tri-O-acetyl-2,6-dideoxy-2-fluoro-5-C-(trifluoromethyl)-α-L-talopyranose 在 碘代三甲硅烷 、 3 A molecular sieve 、 mercury(II) oxide 、 mercury(II) iodide 作用下， 以 1,2-二氯乙烷 、 甲苯 为溶剂， 反应 24.5h， 生成 7-O-(3,4-di-O-acetyl-2,6-dideoxy-2-fluoro-5-C-(trifluoromethyl)-α-L-talopyranosyl)daunomycinone
  参考文献：
  名称：

  7-O- [2,6-二脱氧-2-氟-5-C-（三氟甲基）-α-L-talopyranosyl]-金牛霉素和-阿霉素的合成及其抗肿瘤活性。

  摘要：

  通过3,4-二-O-乙酰基的偶联制得7-O- [2,6-二脱氧-2-氟-5-C-（三氟甲基）-α-L-talopyranosyl]-道诺霉素和-阿霉素-2，6-二脱氧-2-氟-5-C-（三氟甲基）-α-L-talopyranosyl碘化物与道诺霉素。该合成的关键步骤是甲基α-D-lyxopyranoside的区域选择性氟化，得到4-deoxy-4-fluoro-beta-L-ribopyranoside，以及醛-L-核糖衍生物的C-三氟甲基化得到1 ，1,1-三氟-5-单氟-L-麦芽糖醇衍生物。将合成产物的抗肿瘤活性与2'-脱氧-2'-氟和2'，6'-二脱氧-5'-C-三氟甲基类似物的抗肿瘤活性进行了比较。

  DOI：

  10.1016/s0008-6215(99)00028-2
• 作为产物：
  描述：

  Acetic acid (2S,3R,4S,5S)-3,4-bis-benzyloxy-2,6,6,6-tetrafluoro-5-trifluoromethanesulfonyloxy-hexyl ester 在 palladium on activated charcoal 吡啶 、 草酰氯 、 Dowex 50WX₂ (H⁺-form) 、 氢气 、 sodium methylate 、 二甲基亚砜 、 N,N-二异丙基乙胺 、 sodium nitrite 作用下， 以 1,4-二氧六环 、 甲醇 、 水 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 47.0h， 生成 1,3,4-tri-O-acetyl-2,6-dideoxy-2-fluoro-5-C-(trifluoromethyl)-α-L-talopyranose
  参考文献：
  名称：

  7-O- [2,6-二脱氧-2-氟-5-C-（三氟甲基）-α-L-talopyranosyl]-金牛霉素和-阿霉素的合成及其抗肿瘤活性。

  摘要：

  通过3,4-二-O-乙酰基的偶联制得7-O- [2,6-二脱氧-2-氟-5-C-（三氟甲基）-α-L-talopyranosyl]-道诺霉素和-阿霉素-2，6-二脱氧-2-氟-5-C-（三氟甲基）-α-L-talopyranosyl碘化物与道诺霉素。该合成的关键步骤是甲基α-D-lyxopyranoside的区域选择性氟化，得到4-deoxy-4-fluoro-beta-L-ribopyranoside，以及醛-L-核糖衍生物的C-三氟甲基化得到1 ，1,1-三氟-5-单氟-L-麦芽糖醇衍生物。将合成产物的抗肿瘤活性与2'-脱氧-2'-氟和2'，6'-二脱氧-5'-C-三氟甲基类似物的抗肿瘤活性进行了比较。

  DOI：

  10.1016/s0008-6215(99)00028-2

文献信息

• Anthracycline derivative having a trifluoromethylated sugar
  申请人：Zaidan Hojin Biseibutsu Kagaku Kenkyu Kai

  公开号：US05719130A1

  公开（公告）日：1998-02-17

  Novel anthracycline derivatives have now been produced, which exhibit higher antitumor activities and lower toxicities than those of daunomycin, adriamycin etc. that have been clinically used as anticancer agents. That is, a daunomycinone or adriamycinone derivative represented by the general formula (I): ##STR1## wherein R is a hydrogen atom or a hydroxyl group.

  现在已经生产出新型蒽环喜树碱衍生物，其抗肿瘤活性更高，毒性更低，比诸如多柔比星、阿霉素等已经临床使用的抗癌药物更优。换句话说，一种由通用式(I)代表的多柔比星醌或阿霉素醌衍生物已经被制造出来：##STR1## 其中R为氢原子或羟基。
• Fluorine-containing anthracycline derivatives having hydroxyl groups(s)
  申请人：Zaidan Hojin Biseibutsu Kagaku Kenkyu Kai

  公开号：US05789386A1

  公开（公告）日：1998-08-04

  To provide novel fluorine-containing anthracycline derivatives having high antitumor activities and a solubility in water, there have now been synthesized a 7-O-(2,6-dideoxy-2-fluoro-3-O- or -4-O- or -3,4-di-O-aminoalkanoyl-.alpha.-L-talopyranosyl)daunomycinone or -adriamycinone of general formula (I) shown below, as well as a 7-O-(3-O- or -4-O- or -3,4-di-O-aminoalkanoyl-2,6-dideoxy-2,6,6,6-tetrafluoro-.alpha.-L-talopyra nosyl- or -2,6-dideoxy-6,6,6-trifluoro-.alpha.-L-lyxo-hexopyranosyl)adriamycinone of general formula (II) shown below: General formula (I) ##STR1## General formula (II) ##STR2## wherein either one or both of A.sup.1 and A.sup.2 is or are an .alpha.-amino acid residue or an .omega.-amino acid residue and T denotes a fluorine or hydrogen atom. The novel fluorine-containing anthracycline derivatives of general formulae (I) and (II) are highly active against tumors and soluble in water, and they are useful as antitumor agents administrable in the form of injectable solution.

  为了提供具有高抗肿瘤活性和水溶性的新型含氟蒽环素衍生物，已合成了如下所示的通用式(I)的7-O-(2,6-二去氧-2-氟-3-O-或-4-O-或-3,4-二-O-氨基烷酰-α-L-戊糖苷)多柔比星醌或阿霉素醌，以及如下所示的通用式(II)的7-O-(3-O-或-4-O-或-3,4-二-O-氨基烷酰-2,6-二去氧-2,6,6,6-四氟-α-L-戊糖苷-或-2,6-二去氧-6,6,6-三氟-α-L-利克糖苷)阿霉素醌：通用式(I) ##STR1## 通用式(II) ##STR2## 其中A^1和A^2中的一个或两个是α-氨基酸残基或ω-氨基酸残基，T表示氟或氢原子。通用式(I)和(II)的新型含氟蒽环素衍生物对肿瘤具有很高的活性，并且在水中溶解，它们可作为抗肿瘤剂以注射溶液的形式使用。
• NOVEL ANTHRACYCLINE DERIVATIVES CONTAINING TRIFLUOROMETHYLATED SUGAR UNIT
  申请人：ZAIDAN HOJIN BISEIBUTSU KAGAKU KENKYU KAI

  公开号：EP0749976A1

  公开（公告）日：1996-12-27

  Novel anthracycline derivatives have now been produced, which exhibit higher antitumor activities and lower toxicities than those of daunomycin, adriamycin etc. that have been clinically used as anticancer agents. That is, a daunomycinone or adriamycinone derivative represented by the general formula (I): wherein R is a hydrogen atom or a hydroxyl group, and 7-O-(2,6-dideoxy-6,6,6-trifluoro-α-L-lyxo-hexopyranosyl)adriamycinone derivative which is an adriamycinone derivative represented by formula (II): have now been newly synthesized. The novel anthracycline derivatives having the general formula (I) and formula (II), respectively, show excellent anticancer or antitumor activities and are of low toxicities. These novel compounds are very useful as anticancer or antitumor agents and are expected to be useful for the therapeutic treatments of a variety of cancers and tumors, similarly to daunomycin or adriamycin.

  目前已生产出新型蒽环类衍生物，与临床上用作抗癌剂的达霉素、阿霉素等相比，它们具有更高的抗肿瘤活性和更低的毒性。即由通式（I）代表的达霉素酮或阿霉素酮衍生物： 其中 R 是氢原子或羟基，7-O-(2,6-二脱氧-6,6,6-三氟-α-L-来苏己吡喃糖基)阿霉素酮衍生物是由式（II）表示的阿霉素酮衍生物： 的阿霉素衍生物。 分别具有通式(I)和式(II)的新型蒽环类衍生物显示出卓越的抗癌或抗肿瘤活性，而且毒性低。这些新型化合物作为抗癌剂或抗肿瘤剂非常有用，有望与达霉素或阿霉素类似，用于各种癌症和肿瘤的治疗。
• Fluorine-containing anthracycline derivatives having hydroxyl group(s) mono- or di-o-aminoalkanoylated in the sugar moiety thereof
  申请人：ZAIDAN HOJIN BISEIBUTSU KAGAKU KENKYU KAI

  公开号：EP0761678A1

  公开（公告）日：1997-03-12

  To provide novel fluorine-containing anthracycline derivatives having high antitumor activities and a solubility in water, there have now been synthesized a 7-O-(2,6-dideoxy-2-fluoro-3-O- or -4-O- or -3,4-di-O-aminoalkanoyl-α-L-talopyranosyl)daunomycinone or -adriamycinone of general formula (I) shown below, as well as a 7-O-(3-O- or -4-O-or -3,4-di-O-aminoalkanoyl-2,6-dideoxy-2,6,6,6-tetrafluoro-α-L-talopyranosyl- or -2,6-dideoxy-6,6,6-trifluoro-α-L-lyxo-hexopyranosyl)adriamycinone of general formula (II) shown below:- wherein either one or both of A1 and A2 is or are an α-amino acid residue or an ω-amino acid residue and T denotes a fluorine or hydrogen atom. The novel fluorine-containing anthracycline derivatives of general formulae (I) and (II) are highly active against tumors and soluble in water, and they are useful as antitumor agents administrable in the form of injectable solution.

  为了提供具有高抗肿瘤活性和水溶性的新型含氟蒽环类衍生物，现已合成了通式(I)如下的7-O-(2,6-二脱氧-2-氟-3-O-或-4-O-或-3,4-二-O-氨基烷酰基-α-L-吡喃甘露糖基)daunomycinone或-adriamycinone、以及下表所示通式(II)的 7-O-(3-O-或-4-O-或-3,4-二-O-氨基烷酰基-2,6-二脱氧-2,6,6,6-四氟-α-L-吡喃他酰胺基-或-2,6-二脱氧-6,6,6-三氟-α-L-来苏己吡喃糖基)阿霉素酮：- 其中 A1 和 A2 中的一个或两个是 α-氨基酸残基或 ω-氨基酸残基，T 表示氟原子或氢原子。通式(I)和(II)的新型含氟蒽环类衍生物具有很强的抗肿瘤活性，可溶于水，可作为抗肿瘤药物以注射液的形式给药。
• ANTHRACYCLINE DERIVATIVES CONTAINING TRIFLUOROMETHYLATED SUGAR UNIT
  申请人：ZAIDAN HOJIN BISEIBUTSU KAGAKU KENKYU KAI

  公开号：EP0749976B1

  公开（公告）日：1999-04-28