diethyl 2,3-O-isobutylidene-D-tartrate | 872979-93-6

• 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: diethyl 2,3-O-isobutylidene-D-tartrate
• 英文别名: diethyl (4S,5S)-2-propan-2-yl-1,3-dioxolane-4,5-dicarboxylate
• CAS: 872979-93-6
• 化学式: C₁₂H₂₀O₆
• 分子量: 260.287
• InChiKey: QKAAWFQMWNTBAB-IUCAKERBSA-N

物化性质

• 沸点：
  309.2±37.0 °C(Predicted)
• 密度：
  1.126±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 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：

  diethyl 2,3-O-isobutylidene-D-tartrate 以68%的产率得到2,3-O-isobutylidene-D-threitol
  参考文献：
  名称：

  Platinum(II) complex and processes for preparing the same

  摘要：

  本文披露了具有强效抗肿瘤活性的新型铂（II）配合物，其化学式为（1），其中R.sub.1和R.sub.2，可以相同也可以不同，分别为氢原子或C.sub.1-4烷基基团，或者与连接的碳原子共同形成环烷基基团；两个X共同形成由化学式（a）或（b）表示的基团，其中，R.sub.3为氢原子或甲基基团；R.sub.4和R.sub.5，可以相同也可以不同，分别为氢原子或C.sub.1-4烷基基团，或者与碳原子共同形成环丁烷基团；以及4,5-双(氨甲基)-1,3-二氧杂环戊烷基团中各立体中心的绝对构型为（4R,5R）或（4S,5S）；制备这些配合物的方法；以及它们用于治疗动物或人类癌症的用途。此外，本文还披露了用于制备铂（II）配合物的新型中间体以及制备这些中间体的方法。

  公开号：

  US05395947A1
• 作为产物：
  描述：

  D-(-)-酒石酸二乙酯 、 异丁醛 在 甲烷磺酸 作用下， 以 环己烷 为溶剂， 生成 diethyl 2,3-O-isobutylidene-D-tartrate
  参考文献：
  名称：

  Synthesis, anticancer activity and toxicity of a water-soluble 4S,5S-derivative of heptaplatin, cis-{Pt(II)[(4S,5S)-4,5-bis(aminomethyl)-2-isopropyl-1,3-dioxolane]·(3-hydroxyl-cyclobutane-1,1-dicarboxylate)}

  摘要：

  A water-soluble 4S,5S-derivative of heptaplatin, cis-{Pt(II)[(4S,5S)-4,5-bis(aminomethyl)-2-isopropyl-1,3-dioxolane]center dot(3-hydroxyl-cyclobutane-1,1-dicarboxylate)} was synthesized. The anticancer activity and toxicity were evaluated by comparing its interaction with DNA, cytotoxicity against four human cancer cell lines, antitumor efficiency in human gastric carcinoma NCI-N87 xenografts in nude mice, and preliminary side-effects in rats to those of its 4R,5R-optical isomer which is under preclinical development. Both isomers induce condensation of DNA to the same extent and have similar cytotoxicity, but show different antitumor activity and toxicity, probably owing to the difference in respective pharmacokinetic profiles. 4S,5S-Isomer seems to exhibit superior antitumor activity and less toxicity than 4R,5R-optical isomer as well as the parent heptaplatin. These results imply that 4S,5S-configuration as a new drug candidate may be better than 4R,5R-counterpart. (C) 2014 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.jinorgbio.2014.07.013

文献信息

• NOVEL PLATINUM(II) COMPLEX AND PROCESSES FOR PREPARING THE SAME
  申请人：SUNKYONG INDUSTRIES LTD.

  公开号：EP0586378A1

  公开（公告）日：1994-03-16
• US5395947A
  申请人：——

  公开号：US5395947A

  公开（公告）日：1995-03-07
• [EN] NOVEL PLATINUM(II) COMPLEX AND PROCESSES FOR PREPARING THE SAME
  申请人：——

  公开号：WO1992016539A1

  公开（公告）日：1992-10-01

  [EN] Disclosed herein are novel platinum(II) complexe having a potent anti-tumor activity which are represented by formula (1), wherein R1 and R2, which may be the same or different, are a hydrogen atom or a C1-4 alkyl group, respectively, or jointly form a cycloalkane group together with the carbon atom attached thereto; two Xs jointly form a group represented by formula (a) or (b) wherein, R3 is a hydrogen atom or a methyl group; R4 and R5, which may be the same or different, are a hydrogen atom or a C1-4 alkyl group, respectively, or jointly form a cyclobutane together with the carbon thereto; and the absolute configurations at the respective chiral centers in the 4,5-bis(aminomethyl)-1,3-dioxolane moiety are (4R, 5R) or (4S, 5S); processes for preparing the same; and their use for treating animal or human cancer. Further, disclosed herein are novel intermediates useful for the preparation of the platinum(II) complexes and processes for preparing said intermediates.
  [FR] Nouveaux complexes de platine (II) présentant une puissante activité antitumorale et répondant à la formule (I), dans laquelle R1 et R2 sont identiques ou différents et représentent un atome d'hydrogène ou un groupe alkyle C1-4 respectivement, ou forment ensemble un groupe cycloalcane conjointement avec l'atome de carbone lié à celui-ci; les deux X forment ensemble un groupe répondant à la formule (a) ou (b), dans laquelle R3 représente un atome d'hydrogène ou un groupe méthyle; R4 et R5 sont identiques ou différents et représentent un atome d'hydrogène ou un groupe alkyle C1-4 respectivement, ou forment ensemble un cyclobutane conjointement avec l'atome de carbone lié à celui-ci; et les configurations absolues au niveau des centres chiraux respectifs dans la fraction 4,5-bis(aminométhyl)-1,3-dioxolane sont (4R, 5R) ou (4S), (5S); leurs procédés de préparation; et leur utilisation pour le traitement des cancers chez l'homme et chez les animaux. Par ailleurs, on décrit de nouveaux intermédiaires utilisés pour préparer lesdits complexes de platine (II), ainsi que des procédés de préparation de ces intermédiaires.
• Platinum(II) complex and processes for preparing the same
  申请人：Sunkyong Industries, Ltd.

  公开号：US05395947A1

  公开（公告）日：1995-03-07

  Disclosed herein are novel platinum(II) complexes having a potent anti-tumor activity which are represented by the formula (1), ##STR1## wherein R.sub.1 and R.sub.2, which may be the same or different, are a hydrogen atom or a C.sub.1-4 alkyl group, respectively, or jointly form a cycloalkane group together with the carbon atom attached thereto; two Xs jointly form a group represented by formula (a) or (b) wherein, R.sub.3 is a hydrogen atom or a methyl group; R.sub.4 and R.sub.5, which may be the same or different, are a hydrogen atom or a C.sub.1-4 alkyl group, respectively, or jointly form a cyclobutane together with the carbon thereto; and the absolute configurations at the respective chiral centers in the 4,5-bis(aminomethyl)-1,3-dioxolane moiety are (4R,5R) or (4S,5S); processes for the preparing the same; and their use for treating animal or human cancer. Further, disclosed herein are novel intermediates useful for the preparation of the platinum(II) complexes and processes for preparing said intermediates.

  本文披露了具有强效抗肿瘤活性的新型铂（II）配合物，其化学式为（1），其中R.sub.1和R.sub.2，可以相同也可以不同，分别为氢原子或C.sub.1-4烷基基团，或者与连接的碳原子共同形成环烷基基团；两个X共同形成由化学式（a）或（b）表示的基团，其中，R.sub.3为氢原子或甲基基团；R.sub.4和R.sub.5，可以相同也可以不同，分别为氢原子或C.sub.1-4烷基基团，或者与碳原子共同形成环丁烷基团；以及4,5-双(氨甲基)-1,3-二氧杂环戊烷基团中各立体中心的绝对构型为（4R,5R）或（4S,5S）；制备这些配合物的方法；以及它们用于治疗动物或人类癌症的用途。此外，本文还披露了用于制备铂（II）配合物的新型中间体以及制备这些中间体的方法。
• Synthesis, anticancer activity and toxicity of a water-soluble 4S,5S-derivative of heptaplatin, cis-{Pt(II)[(4S,5S)-4,5-bis(aminomethyl)-2-isopropyl-1,3-dioxolane]·(3-hydroxyl-cyclobutane-1,1-dicarboxylate)}
  作者：Weiping Liu、Jing Jiang、Chengying Xie、Shuqian Hou、Haitian Quan、Qingsong Ye、Liguang Lou

  DOI：10.1016/j.jinorgbio.2014.07.013

  日期：2014.11

  A water-soluble 4S,5S-derivative of heptaplatin, cis-Pt(II)[(4S,5S)-4,5-bis(aminomethyl)-2-isopropyl-1,3-dioxolane]center dot(3-hydroxyl-cyclobutane-1,1-dicarboxylate)} was synthesized. The anticancer activity and toxicity were evaluated by comparing its interaction with DNA, cytotoxicity against four human cancer cell lines, antitumor efficiency in human gastric carcinoma NCI-N87 xenografts in nude mice, and preliminary side-effects in rats to those of its 4R,5R-optical isomer which is under preclinical development. Both isomers induce condensation of DNA to the same extent and have similar cytotoxicity, but show different antitumor activity and toxicity, probably owing to the difference in respective pharmacokinetic profiles. 4S,5S-Isomer seems to exhibit superior antitumor activity and less toxicity than 4R,5R-optical isomer as well as the parent heptaplatin. These results imply that 4S,5S-configuration as a new drug candidate may be better than 4R,5R-counterpart. (C) 2014 Elsevier Inc. All rights reserved.