[(4R,5R)-2,2-二甲基-1,3-二氧戊环-4,5-二基]二(亚甲基)二甲烷磺酸酯 | 109281-59-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: [(4R,5R)-2,2-二甲基-1,3-二氧戊环-4,5-二基]二(亚甲基)二甲烷磺酸酯
• 中文别名: (+)-2,3-O-异亚丙基-D-苏糖醇1,4-二甲烷磺酸酯
• 英文名称: 2,3-O-Isopropylidene-1,4-bis-O-(methylsulfonyl)-D-threitol
• 英文别名: (2R,3R)-2,3-O-isopropylidene-1,2,3,4-butanetetraol 1,4-dimethanesulfonate；2,3-O-isopropylidene-1,4-di-O-methanesulphonyl-D-threitol；2,3-O-isopropylidene-D-threitol 1,4-bis(methanesulfonate)；[(4R,5R)-2,2-dimethyl-5-(methylsulfonyloxymethyl)-1,3-dioxolan-4-yl]methyl methanesulfonate
• CAS: 109281-59-6
• 化学式: C₉H₁₈O₈S₂
• 分子量: 318.369
• InChiKey: LIIWJXAZDNSJSP-HTQZYQBOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  122
• 氢给体数：
  0
• 氢受体数：
  8

安全信息

• 海关编码：
  2932999099

反应信息

• 作为反应物：
  描述：

  [(4R,5R)-2,2-二甲基-1,3-二氧戊环-4,5-二基]二(亚甲基)二甲烷磺酸酯 在 palladium on activated charcoal sodium azide 、 氢气 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 ((4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-diyl)dimethanamine
  参考文献：
  名称：

  Analogs of cisplatin derived from diaminodideoxytetritols. Synthesis and activity against the ADJ/PC6 plasmacytoma in mice

  摘要：

  Four new analogues of the anticancer drug cisplatin have been prepared that contain a diaminodideoxytetritol derivative as the amine ligand moiety, and their activities have been measured against the ADJ/PC6 plasmacytoma in mice. Two of these compounds, the enantiomers of cis-dichloro(1,4-diamino-1,4-dideoxy-2,3-O-isopropylidenethreitol) -platinum(II) , show a higher TI value than cisplatin when administered by intraperitoneal injection and, importantly, show significant antitumour activity when administered orally.

  DOI：

  10.1021/jm00124a004
• 作为产物：
  描述：

  (-)-二甲基-2,3-邻异丙亚基-L-酒石酸酯 在 sodium tetrahydroborate 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 [(4R,5R)-2,2-二甲基-1,3-二氧戊环-4,5-二基]二(亚甲基)二甲烷磺酸酯
  参考文献：
  名称：

  Combination of chemotherapy and oxidative stress to enhance cancer cell apoptosis

  摘要：

  1,2-二硒环戊烷单元是构建依赖谷胱甘肽的前药的通用支架，表现出对癌细胞增强的效力，并通过化疗和氧化应激的组合发挥作用。

  DOI：

  10.1039/c9sc05997k

文献信息

• Chiroptical properties of 2,2’-bioxirane
  作者：N. Daugey、N. De Rycke、T. Brotin、T. Buffeteau

  DOI：10.1002/chir.22814

  日期：2018.4

  The two enantiomers of 2,2′‐bioxirane were synthesized, and their chiroptical properties were thoroughly investigated in various solvents by polarimetry, vibrational circular dichroism (VCD), and Raman optical activity (ROA). Density functional theory (DFT) calculations at the B3LYP/aug‐cc‐pVTZ level revealed the presence of three conformers (G+, G−, and cis) with Gibbs populations of 51, 44, and 5%

  合成了2,2'-生物环氧乙烷的两种对映异构体，并通过旋光法，振动圆二色性（VCD）和拉曼光学活性（ROA）在各种溶剂中彻底研究了它们的手性。在B3LYP / AUG-CC-pVTZ水平密度泛函理论（DFT）计算显示三个构象（存在ģ +，g ^ - ，和顺式分别为51，44和5％吉布斯种群的分离的分子，） 。两个主要的构象异构体的人口比例进行了修改为显示更高介电常数（溶剂ģ -形式降低，而G ^ +形式增加）。通过使用可极化连续体模型（PCM），通过与时间有关的DFT计算可以正确地再现特定溶剂在不同旋光度值下的行为，但对于苯，必须使用显式溶剂模型。最后，VCD和ROA光谱完全由DFT / PCM计算为玻尔兹曼平均再现ģ +和G ^ -构象。
• 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。
• Platinum coordination compounds
  申请人：Johnson Matthey Public Limited Company

  公开号：US04783452A1

  公开（公告）日：1988-11-08

  Coordination compounds of platinum(II) with 4,5-bis(aminomethyl)-1,3-dioxolane, intended for use in the treatment of cancer. The compounds may exist as monomers or as linear or cyclic polymers.

  铂(II)与4,5-双(氨甲基)-1,3-二氧杂环戊烷形成的配合物，用于治疗癌症。这些化合物可以存在为单体或线性或环状聚合物。
• Interstrand and Intrastrand DNA−DNA Cross-Linking by 1,2,3,4-Diepoxybutane:  Role of Stereochemistry
  作者：Soobong Park、Christopher Anderson、Rachel Loeber、Mahadevan Seetharaman、Roger Jones、Natalia Tretyakova

  DOI：10.1021/ja051979x

  日期：2005.10.1

  1,2,3,4-Diepoxybutane (DEB) is a bifunctional electrophile capable of forming DNA-DNA and DNA-protein cross-links. DNA alkylation by DEB produces N7-(2'-hydroxy-3',4'-epoxybut-1'-yl)-guanine monoadducts, which can then form 1,4-bis-(guan-7-yl)-2,3-butanediol (bis-N7G-BD) lesions. All three optical isomers of DEB are produced metabolically from 1,3-butadiene, but S,S-DEB is the most cytotoxic and genotoxic. In the present work, interstrand and intrastrand DNA-DNA cross-linking by individual DEB stereoisomers was investigated by PAGE, mass spectrometry, and stable isotope labeling. S,S-, R,R-, and meso-diepoxides were synthesized from L-dimethyl-2,3-O-isopropylidene-tartrate, D-dimethyl-2,3-O-isopropyl id e ne-tart rate, and meso-erythritol, respectively. Total numbers of bis-N7G-BD lesions (intrastrand and interstrand) in calf thymus DNA treated separately with S,S-, R,R-, or meso-DEB (0.01-0.5 mM) were similar as determined by capillary HPLC-ESI+-MS/MS of DNA hydrolysates. However, denaturing PAGE has revealed that S,S-DEB produced the highest number of interchain cross-links in 5'-GGC-3/3'-CCG-5' sequences. Intrastrand adduct formation by DEB was investigated by a novel methodology based on stable isotope labeling HPLC-ESI+-MS/MS. Meso DEB treatment of DNA duplexes containing 5'-[1,7,NH2-N-15(3),2-C-13-G]GC-3'/3'-CCG-5' and 5'-GGC-3/3'-CC[N-15(3),2-C-13-G]-5' trinucleotides gave rise to comparable numbers of 12-intrastrand and 1,3-interstrand bis-N7G-BD cross-links, while S,S DEB produced few intrastrand lesions. R,P-DEB treated DNA contained mostly 1,3-interstrand bis-N7G-BD, along with smaller amounts of 1,2-interstrand and 1,2-intrastrand adducts. The effects of DEB stereochemistry on its ability to form DNA-DNA cross-links may be rationalized by the spatial relationships between the epoxy alcohol side chains in stereoisomeric N7-(2'-hydroxy-3',4'-epoxybut-1'-yl)-guanine adclucts and their DNA environment. Different cross-linking specificities of DEB stereoisomers provide a likely structural basis for their distinct biological activities.
• Ring-Opening and -Expansion of 2,2′-Biaziridine: Access to Diverse Enantiopure Linear and Bicyclic Vicinal Diamines
  作者：Stephen J. Bailey、Steven M. Wales、Anthony C. Willis、Paul A. Keller

  DOI：10.1021/ol502164b

  日期：2014.8.15

  The chiral pool-derived 1,1'-ditosyl-2,2'-biaziridine has been established as a valuable building block for the divergent synthesis of enantiopure vicinal diamines. Efficient procedures for the regioselective ring opening of the biaziridine with oxygen, sulfur, nitrogen, and carbon nucleophiles are described. The strategic use of nucleophiles bearing pendant functionality allows further elaboration of the acyclic products to a variety of 2,2'-bicyclic-embedded diamines. Desymmetrization of the biaziridine has also been accomplished via the selective monoaddition of organocuprates.