2R,3R-1,4-diamino-2,3-butanediol | 118712-69-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2R,3R-1,4-diamino-2,3-butanediol
• 英文别名: (2R,3R)-1,4-Diamino-2,3-butan-diol；(2R,3R)-1,4-diaminobutane-2,3-diol
• CAS: 118712-69-9
• 化学式: C₄H₁₂N₂O₂
• 分子量: 120.151
• InChiKey: HYXRUUHQXNAFAJ-QWWZWVQMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.9
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  92.5
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 二硝基氟甲烷 、 2R,3R-1,4-diamino-2,3-butanediol 生成 (meso)-1,10-Difluor-1,1,3,8,10,10-hexanitro-3,8-diaza-5,6-decandiol Dinitrat
  参考文献：
  名称：

  N-(2-fluoro-2, 2-dinitroethyl)-N-nitroamino alcohols and some of their derivatives

  摘要：

  DOI：

  10.1007/bf00852670
• 作为产物：
  描述：

  (R,R)-1,4-Diamethan-sulfonamido-2,3-butan-diol 在 氢溴酸 作用下， 生成 2R,3R-1,4-diamino-2,3-butanediol
  参考文献：
  名称：

  与2,2'-双氮丙啶有关的烷基化剂。3.立体异构体N，N′-二甲磺酰基-2，2′-二氮丙啶。

  摘要：

  DOI：

  10.1021/jm00297a025

文献信息

• Ringschlussreaktionen des Butadiendioxids mit Hydrazinen zu neuen Derivaten des Pyrazolidins und Piperidazins
  作者：H. R. Meyer、R. Gabler

  DOI：10.1002/hlca.19630460727

  日期：——

  The reaction of butadiene dioxide (dl-and meso-) with various hydrazines led to 1: 1-adducts having either pyrazolidine or piperidazine structures. Using N,N′-di-substituted hydrazines, pyrazolidine derivatives were obtained with yields of 70–80%, whereas hydrazine itself reacted with DL-butadiene dioxide to give about 20% of trans-4,5-dihydroxypiperidazine and a small quantity of trans-7,8-tetrah

  丁二烯二氧化物（dl-和内消旋-）与各种肼的反应产生具有吡唑烷或哌啶嗪结构的1：1加合物。使用N，N'-二取代肼，可获得吡唑烷衍生物，产率为70-80％，而肼本身与DL-丁二烯反应生成约20％的反式-4,5-二羟基哌啶嗪和少量反式-7，8-四羟基-10-氮杂喹唑嗪。五环闭合反应似乎是一般的制备性有趣的吡唑烷合成。通过将5-环和6-环系统转化为开链二胺来证明其结构。这些二胺的组成是通过独立合成或转化成已知化合物来确定的。通过NMR分析分别将其他1∶1-加合物分配给吡唑烷或哌啶氮烷系列。
• Petrov,A.S. et al., Journal of general chemistry of the USSR, 1974, vol. 44, p. 1109 - 1113
  作者：Petrov,A.S. et al.

  DOI：——

  日期：——
• Mutagenic Spectrum of Butadiene-Derived <i>N</i>1-Deoxyinosine Adducts and <i>N</i>⁶,<i>N</i>⁶-Deoxyadenosine Intrastrand Cross-Links in Mammalian Cells
  作者：Manorama Kanuri、Lubomir V. Nechev、Pamela J. Tamura、Constance M. Harris、Thomas M. Harris、R. Stephen Lloyd

  DOI：10.1021/tx025591g

  日期：2002.12.1

  Reactive metabolites of 1,3-butadiene, including 1,2-epoxy-3-butene (BDO), 1,2:3,4-diepoxybutane (BDO2), and 3,4-epoxy-1,2-butanediol (BDE), form both stable and unstable base adducts in DNA and have been implicated in producing genotoxic effects in rodents and human cells. N1 deoxyadenosine adducts are unstable and can undergo either hydrolytic deamination to yield N1 deoxyinosine adducts or Dimroth rearrangement to yield N-6 adducts. The dominant point mutation observed at AT sites in both in vivo and in vitro mutagenesis studies using BD and its epoxides has been A --> T transversions followed by A --> G transitions. To understand which of the butadiene adducts are responsible for mutations at AT sites, the present study focuses on the N1 deoxyinosine adduct at C2 of BDO and N-6,N-6-deoxyadenosine intrastrand cross-links derived from BDO2. These lesions were incorporated site-specifically and stereospecifically into oligodeoxynucleotides which were engineered into mammalian shuttle vectors for replication bypass and mutational analyses in COS-7 cells. Replication of DNAs containing the R,R-BDO2 intrastrand cross-link between N-6 positions of deoxyadenosine yielded a high frequency (59%) of single base substitutions at the 3' adducted base, while 19% mutagenesis was detected using the S,S-diastereomer. Comparable studies using the R- and S-diastereomers of the N1 deoxyinosine adduct gave rise to similar to50 and 80% A --> G transitions with overall mutagenic frequencies of 59 and 90%, respectively. Collectively, these data establish a molecular basis for A --> G transitions that are observed following in vivo and in vitro exposures to 131) and its epoxides, but fail to reveal the source of the A --> T transversions that are the dominant point mutation.
• Synthesis and antitumor activity of (2R,3R)-2,3-dihydroxy- and -2,3-dialkoxy-1,4-diaminobutane platinum(II) complexes
  作者：Dae-Kee Kim、Jongsik Gam、Yong-Baik Cho、Hun-Taek Kim、Key H. Kim

  DOI：10.1016/0960-894x(96)00089-3

  日期：1996.3

  The synthesis and antitumor activity of (2R,3R)-2,3-dihydroxy- and -2,3-dialkoxy-1,4-diaminobutane platinum(II) complexes 10-15 are described. cis-Dichloro [(2R,3R)-2,3-dimethoxy-1,4-diaminobutane]platinum(II) (11) and cis-(cyclobutane-1,1-dicarboxylato) [(2R,3R)-2,3-dihydroxy-1,4-diaminobutane]platinum(II) (13) showed the potent antitumor activity against L1210 leukemia in mice with % T/C values of around 200.
• Alkylating agents related to 2,2'-biaziridine. III. Stereoisomeric N,N'-dimethylsulfonyl-2,2'-biaziridines
  作者：Peter W. Feit、Ole T. Nielsen

  DOI：10.1021/jm00297a025

  日期：1970.5