3,6-anhydro-7-O-benzoyl-5-O-benzyl-2-deoxy-7-C-phenyl-D-glycero-D-ido-heptono-1,4-lactone | 1234573-87-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3,6-anhydro-7-O-benzoyl-5-O-benzyl-2-deoxy-7-C-phenyl-D-glycero-D-ido-heptono-1,4-lactone
• 英文别名: [(R)-[(2R,3S,3aS,6aR)-5-oxo-3-phenylmethoxy-3,3a,6,6a-tetrahydro-2H-furo[3,2-b]furan-2-yl]-phenylmethyl] benzoate
• CAS: 1234573-87-5
• 化学式: C₂₇H₂₄O₆
• 分子量: 444.484
• InChiKey: DFXFTZQSJSFULN-XDXGNBCUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3,6-anhydro-7-O-benzoyl-5-O-benzyl-2-deoxy-7-C-phenyl-D-glycero-D-ido-heptono-1,4-lactone 在 碘化钛(IV) 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以55%的产率得到3,6-anhydro-7-O-benzoyl-2-deoxy-7-C-phenyl-D-glycero-D-ido-heptono-1,4-lactone
  参考文献：
  名称：

  在C-7位置带有卤素或叠氮基的新型goniofufurone和7- epi- goniofufurone模拟物的设计，合成和体外抗肿瘤活性

  摘要：

  设计，合成并评估了一系列新的抗肿瘤内酯，这些内酯包含[3.3.0]双环呋喃内酯核心和C-7位置的卤素或叠氮基，并在体外对一组人类肿瘤具有抗肿瘤活性。细胞系。一些类似物对某些人类肿瘤细胞显示出强大的抗增殖作用，但它们都没有对正常胎儿肺成纤维细胞（MRC-5）产生任何细胞毒性。SAR研究表明，这些内酯的结构特征可能会影响其抗增殖活性。它们是：存在于C-7位置的取代基的性质，在C-7位置的立体化学，在C-7位置不存在苯基。流式细胞仪数据表明合成的类似物在K562细胞培养物中的细胞毒性作用是由细胞凋亡介导的，另外揭示了这些分子诱导了这些细胞的细胞周期分布变化。蛋白质印迹分析的结果表明，大多数合成的化合物以半胱天冬酶依赖性方式诱导K562细胞凋亡。

  DOI：

  10.1016/j.ejmech.2017.01.024
• 作为产物：
  描述：

  3-O-苄基-1,2:5,6-O-双异丙叉-α-D-呋喃葡萄糖 在 吡啶 、 sodium tetrahydroborate 、 L-酒石酸 、 高碘酸 、 三乙胺 、 pyridinium chlorochromate 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 99.5h， 生成 3,6-anhydro-7-O-benzoyl-5-O-benzyl-2-deoxy-7-C-phenyl-D-glycero-D-ido-heptono-1,4-lactone
  参考文献：
  名称：

  Heteroannelated and 7-deoxygenated goniofufurone mimics with antitumour activity: Design, synthesis and preliminary SAR studies

  摘要：

  Cytotoxic (+)-goniofufurone mimic such as benzoxepane 2 was preferentially formed after the treatment of 7-O-benzoyl-5-O-benzyl (+)-goniofufurone derivative 6 with titanium(IV) fluoride. However, the corresponding 7-epimer 5 (derivative of 7-epi-goniofufurone) under the similar reaction conditions gave mainly 7-deoxy derivative 7 as a result of an unexpected 1,5-hydride shift. Extension of this methodology to the enantiomer ent-6 provided cytotoxic (-)-goniofufurone mimics ent-2 and ent-7. Synthesized compounds showed diverse growth inhibitory effects against selected tumour cell lines, but were devoid of any significant toxicity towards the normal foetal lung fibroblasts (MRC-5). A SAR study reveals the structural features of these lactones that are beneficial for their antiproliferative activity, such as presence of an additional oxepane ring, the absolute stereochemistry and the presence of a deoxy function at the C-7 position. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.08.069

文献信息

• Design, synthesis and antiproliferative activity of styryl lactones related to (+)-goniofufurone
  作者：Velimir Popsavin、Bojana Srećo、Goran Benedeković、Jovana Francuz、Mirjana Popsavin、Vesna Kojić、Gordana Bogdanović

  DOI：10.1016/j.ejmech.2010.03.010

  日期：2010.7

  This paper describes a straightforward divergent synthesis of (+)-goniofufurone mimics (4, 5 and 6) starting from d-xylose. In a preliminary bioassay, analogues 4 and 5 exhibited a submicromolar antiproliferative activity towards HL-60 cells, while the corresponding parent compound 1 was completely inactive against this cell line. At the same time, these molecules showed approximately 10-fold stronger

  本文描述的（+）一个简单的发散合成- goniofufurone模拟物（4，5和6）从起始d木糖。在初步的生物测定中，类似物4和5对HL-60细胞表现出亚微摩尔的抗增殖活性，而相应的母体化合物1对该细胞系完全没有活性。同时，与标准抗癌药阿霉素（DOX）相比，这些分子在同一细胞系中显示出约10倍更强的细胞毒性。与对照化合物1相比，类似物6在Raji细胞系中显示出18倍和3倍的效力和DOX分别。还公开了从d-木糖制备（+）-gonfufufurone（1）和（+）-crassalactone C（3）的新的分歧路线。
• Novel goniofufurone and 7-epi-goniofufurone mimics from an unexpected titanium-mediated displacement process
  作者：Jovana Francuz、Bojana Srećo、Mirjana Popsavin、Goran Benedeković、Vladimir Divjaković、Vesna Kojić、Gordana Bogdanović、Agneš Kapor、Velimir Popsavin

  DOI：10.1016/j.tetlet.2012.01.121

  日期：2012.4

  Treatment of 7-O-benzoyl-5-O-benzyl derivatives of (+)-goniofufurone or 7-epi-(+)-goniofufurone with titanium(IV) chloride or titanium(IV) bromide gave 7-chloro and 7-bromo-7-deoxy-goniofufurone mimics as the main reaction products along with minor amounts of the corresponding C-7 epimers. An unexpected cyclized product, benzoxepane 8 was isolated in some cases. (C) 2012 Elsevier Ltd. All rights reserved.
• Design, synthesis and in vitro antitumour activity of new goniofufurone and 7- epi -goniofufurone mimics with halogen or azido groups at the C-7 position
  作者：Jovana Francuz、Ivana Kovačević、Mirjana Popsavin、Goran Benedeković、Bojana Srećo Zelenović、Vesna Kojić、Dimitar Jakimov、Lidija Aleksić、Gordana Bogdanović、Tatjana Srdić-Rajić、Eva Lončar、Marko V. Rodić、Vladimir Divjaković、Velimir Popsavin

  DOI：10.1016/j.ejmech.2017.01.024

  日期：2017.3

  A series of new antitumour lactones containing the [3.3.0] bicyclic furano-lactone core and the halogen or azido group at the C-7 position have been designed, synthesized, and evaluated for their in vitro antitumour activity against a panel of human tumour cell lines. Some of the analogues displayed powerful antiproliferative effects to certain human tumour cells, but all of them were devoid of any

  设计，合成并评估了一系列新的抗肿瘤内酯，这些内酯包含[3.3.0]双环呋喃内酯核心和C-7位置的卤素或叠氮基，并在体外对一组人类肿瘤具有抗肿瘤活性。细胞系。一些类似物对某些人类肿瘤细胞显示出强大的抗增殖作用，但它们都没有对正常胎儿肺成纤维细胞（MRC-5）产生任何细胞毒性。SAR研究表明，这些内酯的结构特征可能会影响其抗增殖活性。它们是：存在于C-7位置的取代基的性质，在C-7位置的立体化学，在C-7位置不存在苯基。流式细胞仪数据表明合成的类似物在K562细胞培养物中的细胞毒性作用是由细胞凋亡介导的，另外揭示了这些分子诱导了这些细胞的细胞周期分布变化。蛋白质印迹分析的结果表明，大多数合成的化合物以半胱天冬酶依赖性方式诱导K562细胞凋亡。
• Heteroannelated and 7-deoxygenated goniofufurone mimics with antitumour activity: Design, synthesis and preliminary SAR studies
  作者：Velimir Popsavin、Jovana Francuz、Bojana Srećo Zelenović、Goran Benedeković、Mirjana Popsavin、Vesna Kojić、Gordana Bogdanović

  DOI：10.1016/j.bmcl.2013.08.069

  日期：2013.10

  Cytotoxic (+)-goniofufurone mimic such as benzoxepane 2 was preferentially formed after the treatment of 7-O-benzoyl-5-O-benzyl (+)-goniofufurone derivative 6 with titanium(IV) fluoride. However, the corresponding 7-epimer 5 (derivative of 7-epi-goniofufurone) under the similar reaction conditions gave mainly 7-deoxy derivative 7 as a result of an unexpected 1,5-hydride shift. Extension of this methodology to the enantiomer ent-6 provided cytotoxic (-)-goniofufurone mimics ent-2 and ent-7. Synthesized compounds showed diverse growth inhibitory effects against selected tumour cell lines, but were devoid of any significant toxicity towards the normal foetal lung fibroblasts (MRC-5). A SAR study reveals the structural features of these lactones that are beneficial for their antiproliferative activity, such as presence of an additional oxepane ring, the absolute stereochemistry and the presence of a deoxy function at the C-7 position. (C) 2013 Elsevier Ltd. All rights reserved.