1-chloro-N,O-di(trifluoroacetyl)daunosamine | 58166-30-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: 1-chloro-N,O-di(trifluoroacetyl)daunosamine
• 英文别名: O,N-bistrifluoroacetyl daunosaminyl chloride；3-trifluoroacetamido-4-O-trifluoroacetyl-2,3,6-trideoxy-α,β-L-lyxopyranosyl chloride；2,3,6-trideoxy-4-O-(trifluoroacetyl)-3-[(trifluoroacetyl)amino]-δ-L-lyxo-hexopyranosyl chloride；[(2S,3S,4S)-6-chloro-2-methyl-4-[(2,2,2-trifluoroacetyl)amino]oxan-3-yl] 2,2,2-trifluoroacetate
• CAS: 58166-30-6
• 化学式: C₁₀H₁₀ClF₆NO₄
• 分子量: 357.637
• InChiKey: YARBQFHYGPNYKO-HPASCFBVSA-N

物化性质

• 沸点：
  354.0±42.0 °C(Predicted)
• 密度：
  1.52±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  1-chloro-N,O-di(trifluoroacetyl)daunosamine 在 silver trifluoromethanesulfonate 作用下， 生成 6-deoxycarminomycin
  参考文献：
  名称：

  区域特异性的6-脱氧蒽环类全合成：6-脱氧卡那霉素

  摘要：

  报道了新型蒽环类6-脱氧卡米霉素（14b）的区域特异性合成：糖苷配基的构建基于区域选择性方式将1,4,5-三甲氧基-3-lithionaphthlene（3）与内酯（9）偶联。，这是一种新的合成方法，可提供通向6-脱氧蒽环素的一般途径。

  DOI：

  10.1039/c39840000530
• 作为试剂：
  描述：

  (7S,9S)9-乙酰基-7,8,9,10-四氢-6,7,9,11-四羟基-5,12-并四苯二酮 、 1-chloro-N,O-di(trifluoroacetyl)daunosamine 在 1-chloro-N,O-di(trifluoroacetyl)daunosamine 作用下， 以43的产率得到
  参考文献：
  名称：

  Experientia. 1978, 34, 1255-1257

  摘要：

  DOI：

文献信息

• [EN] FUNCTIONALIZED MORPHOLINYL ANTHRACYCLINE DERIVATIVES<br/>[FR] DÉRIVÉS DE MORPHOLINYLANTHRACYCLINE FONCTIONNALISÉS
  申请人：NERVIANO MEDICAL SCIENCES SRL

  公开号：WO2016071418A1

  公开（公告）日：2016-05-12

  The present invention relates to new functionalized morpholinyl anthracycline derivatives which have cytotoxic activity and are useful in treating diseases such as cancer, cellular proliferation disorders and viral infections. The present invention also provides methods for preparing these compounds, pharmaceutical compositions comprising them and methods of treating diseases utilizing such compounds, or the pharmaceutical compositions containing them. The invention also relates to the use of these derivatives in the preparation of conjugates. The morpholinyl anthracycline derivatives are of the formula Ant-L-W-Z-RM (I) wherein RM is null or a reactive moiety; Z is null or a peptidic, non peptidic or hybrid - peptidic and non peptidic - linker; W is null or a self-immolative system, comprising one or more self-immolative groups; L is null or a conditionally-cleavable moiety; Ant is an anthracycline moiety selected from the formulas (II), (III), (IV) and (V), wherein the wavy line indicates the attachment to the conditionally-cleavable moiety L, or to the self-immolative system W, or to the linker Z, or to the reactive moiety RM; provided that at least one of L, W, Z and RM is not null; R1 is halogen or NR4R5; R2 is OR6, NR7R8 or an optionally substituted group selected from straight or branched C1C4alkyl-, NR7R8-C1C4alkyl- and R60-C1C4alkyl-; R4 and R5 are independently hydrogen, a monosubstituted-benzyl, a disubstituted-benzyl, or an optionally substituted group selected from straight or branched C1-C6alkyl, NR7R8-C1-C6alkyl-, R60-C1-C6alkyl-, R7R8N-C1-C6alkylcarbonyl-, R60-C1-C6alkylcarbonyl-, R7R8N-C1-C6alkoxycarbonyl- and R60-C1-C6alkoxycarbonyl-; or R4 and R5, taken together with the nitrogen atom to which they are bound, form a heterocyclyl substituted with R4', wherein R4' is hydrogen or a group selected from straight or branched C1-C6alkyl and NR7R8-C1-C6alkyl-; R15 is null or an optionally substituted bivalent group selected from -NR7-C1-C6alkyl*, -O-C1-C6alkyl*, -NR7-C1-C6alkylcarbonyl*, -O-C1-C6alkylcarbonyl*, -NR7-C1-C6alkoxycarbonyl* and -O-C1-C6alkoxycarbonyl*, wherein * indicates the point of attachment to -NH-Ant; R6, R7 and R8 are independently hydrogen or an optionally substituted straight or branched C1-C6alkyl; or a pharmaceutically acceptable salt thereof.

  本发明涉及具有细胞毒活性并用于治疗癌症、细胞增殖紊乱和病毒感染等疾病的新功能化吗啉基蒽环素衍生物。本发明还提供了制备这些化合物的方法、包含它们的药物组合物以及利用这些化合物或含有它们的药物组合物治疗疾病的方法。该发明还涉及将这些衍生物用于制备共轭物的用途。吗啉基蒽环素衍生物的化学式为Ant-L-W-Z-RM（I），其中RM为空或为反应性基团；Z为空或为肽、非肽或混合肽和非肽连接物；W为空或为自解离系统，包括一个或多个自解离基团；L为空或为条件可切割基团；Ant为从化学式（II）、（III）、（IV）和（V）中选择的蒽环素基团，其中波浪线表示与条件可切割基团L、自解离系统W、连接物Z或反应性基团RM的连接；但要求至少有一个L、W、Z和RM不为空；R1为卤素或NR4R5；R2为OR6、NR7R8或从直链或支链C1-C4烷基、NR7R8-C1-C4烷基和R60-C1-C4烷基中选择的可选择取代基团；R4和R5独立地为氢、单取代苄基、双取代苄基或从直链或支链C1-C6烷基、NR7R8-C1-C6烷基、R60-C1-C6烷基、R7R8N-C1-C6烷基羰基、R60-C1-C6烷基羰基、R7R8N-C1-C6烷氧羰基和R60-C1-C6烷氧羰基中选择的可选择取代基团；或R4和R5与它们结合的氮原子一起形成与R4'取代的杂环烷基，其中R4'为氢或从直链或支链C1-C6烷基和NR7R8-C1-C6烷基中选择的基团；R15为空或从-NR7-C1-C6烷基*、-O-C1-C6烷基*、-NR7-C1-C6烷基羰基*、-O-C1-C6烷基羰基*、-NR7-C1-C6烷氧羰基*和-O-C1-C6烷氧羰基*中选择的可选择取代的二价基团，其中*表示与-NH-Ant的连接点；R6、R7和R8独立地为氢或可选择取代的直链或支链C1-C6烷基；或其药学上可接受的盐。
• The synthesis of daunosaminyl ε-rhodomycinone, daunosaminyl 10-epi-ε-rhodomycinone, daunosaminyl ε-pyrromycinone, and 10-descarbomethoxy-ε-pyrromycin
  作者：John M. Essery、Terrence W. Doyle

  DOI：10.1139/v80-295

  日期：1980.9.1

  The epimerisation at C10 of ε-rhodomycinone by aqueous alkali treatment of its 6,7-acetonide is described. Daunosaminyl ε-rhodomycinone and daunosaminyl 10-epi-ε-rhodomycinone were prepared and compared with regard to their antibacterial properties. Daunosaminyl ε-pyrromycinone and 10-descarbomethoxy-ε-pyrromycin were synthesized and their antitumor properties were compared with some naturally occurring glycosides of ε-pyrromycinone.

  通过对6,7-缩醛衍生物进行水性碱处理，描述了ε-罗多霉素酮C10的顺式异构化。制备了达诺霉胺基ε-罗多霉素酮和达诺霉胺基10-顺式异构体ε-罗多霉素酮，并比较了它们的抗菌性能。合成了达诺霉胺基ε-吡啶霉素酮和10-脱羧甲氧基-ε-吡啶霉素，并将它们的抗肿瘤性能与一些天然产生的ε-吡啶霉素酮糖苷进行了比较。
• Stereospecific total synthesis of 9-aminoanthracyclines: (+)-9-amino-9-deoxydaunomycin and related compounds
  作者：Kikuo Ishizumi、Naohito Ohashi、Norihiko Tanno

  DOI：10.1021/jo00229a010

  日期：1987.10
• Jizba, Josef V.; Sedmera, Petr; Prikrylova, Vera, Collection of Czechoslovak Chemical Communications, 1989, vol. 54, # 4, p. 1104 - 1117
  作者：Jizba, Josef V.、Sedmera, Petr、Prikrylova, Vera、Vokoun, Jindrich、Mikulik, Karel、Vanek, Zdenko

  DOI：——

  日期：——
• JIZBA, JOSEF V.;SEDMERA, PETR;PRIKRYLOVA, VERA;VOKOUN, JINDRICH;MIKULIK, +, COLLECT. CZECHOSL. CHEM. COMMUN., 54,(1989) N, C. 1104-1117
  作者：JIZBA, JOSEF V.、SEDMERA, PETR、PRIKRYLOVA, VERA、VOKOUN, JINDRICH、MIKULIK, +

  DOI：——

  日期：——