2,3-二氨基-1,4-丁二醇 | 136598-06-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 2,3-二氨基-1,4-丁二醇
• 英文名称: (2R,3R)-2,3-diamino-1,4-butanediol
• 英文别名: 2,3-diamino-2,3-dideoxy-D-threitol；(2R,3R)-2,3-Diaminobutane-1,4-diol
• CAS: 136598-06-6
• 化学式: C₄H₁₂N₂O₂
• 分子量: 120.151
• InChiKey: JOINEDRPUPHALH-IMJSIDKUSA-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：

  2-(叔丁氧羰基氧亚氨基)-2-苯乙腈 、 2,3-二氨基-1,4-丁二醇 在 三乙胺 作用下， 以 水 为溶剂， 反应 8.0h， 以55%的产率得到(2R,3R)-2,3-bis(tert-butyoxycarbonylamino)-1,4-butanediol
  参考文献：
  名称：

  Cyclic Disulfide C(8) Iminoporfiromycin:  Nucleophilic Activation of a Porfiromycin

  摘要：

  The clinical success of mitomycin C (1) and its associated toxicities and resistance have led to efforts to prepare semisynthetic analogues (i.e., KW-2149 (3), BMS-181174 (4)) that have improved pharmacological profiles. In this study, we report the preparation and evaluation of the novel 7-N-(1'-amino-4',5'-dithian-2'-yl)porfiromycin C(8) cyclized imine (6) and its reference compound, 7-N-(1'-aminocyclohex-2'-yl)porfiromycin C(8) cyclized imine (13). Porfiromycin 6 contains a disulfide unit that, upon cleavage, may provide thiol(s) that affect drug reactivity. We demonstrated that phosphines dramatically accelerated 6 activation and solvolysis in methanolic solutions ("pH 7.4") compared with 13. Porfiromycins 6 and 13 efficiently cross-linked EcoRI-linearized pBR322 DNA upon addition of Et3P. We found enhanced levels of interstrand cross-link (ISC) adducts for 6 and 13 compared with porfiromycin (7) and that 6 was more efficient than 13. The large Et3P-mediated rate enhancements for the solvolysis of 6 compared with 13 and a N(7)-substituted analogue of 1, and the increased levels of ISC adducts for 6 compared with 13 and 7 are attributed to a nucleophile-assisted disulfide cleavage process that permits porfiromycin activation and nucleophile (MeOH, DNA) adduction. The in vitro antiproliferative activities of 6 and 13 using the A549 tumor cell line (lung adenocarcinoma) were determined under aerobic and hypoxic conditions and then compared with 7. Both 6 and 13 were more cytotoxic than 7, with 13 being more potent than 6. The C(8) iminoporfiromycins 6 and 13 displayed anticancer profiles similar to 3.

  DOI：

  10.1021/ja030577r
• 作为产物：
  描述：

  (2R*,3S*)-1,4-bis(benzyloxy)butane-2,3-diol 生成 2,3-二氨基-1,4-丁二醇
  参考文献：
  名称：

  与2,2'-双氮丙啶有关的烷基化剂。二。N，N′-二甲乙氧基-2，2′-二氮丙啶。

  摘要：

  DOI：

  10.1021/jm00317a039

文献信息

• Efficient synthesis of (2R,3R)- and (2S,3S)-2,3-diaminobutane-1,4-diol and their dibenzyl ethers
  作者：Andreas Scheurer、Paul Mosset、Rolf W Saalfrank

  DOI：10.1016/s0957-4166(97)00086-4

  日期：1997.4

  (2R,3R)-2,3-Diaminobutane-1,4-diol 6 and its dibenzyl ether 7 were efficiently synthesized starting from L-tartaric acid 1a. The crucial step, debenzylation of intermediate dibenzyloxydiazide 4, was accomplished in good yield by boron trichloride-dimethyl sulfide complex. The enantiomeric series was similarly obtained starting from D-tartaric acid.

  （2 - [R，3 - [R）-2,3-二氨基丁烷-1,4-二醇6和它的二苄基醚7被有效地合成从L-酒石酸起始1A。关键步骤是中间体二苄氧基二叠氮化物4的脱苄基反应，是通过三氯化硼-二甲基硫醚络合物以高收率完成的。从D-酒石酸类似地获得对映体系列。
• Synthesis of diaminodideoxyalditol analogs of cisplatin as antitumor agents
  作者：S. Hanessian、J.-Y. Gauthier、K. Okamoto、A.L. Beauchamp、T. Theophanides

  DOI：10.1139/v93-117

  日期：1993.6.1

  Acyclic vicinal polyol complexes related to cisplatin were synthesized from D-mannitol by stereocontrolled manipulation of the hydroxy groups. Controlled cleavage of a 3,4-diazido hexitol gave the corresponding D-threitol and D-xylitol analogs, which were converted to their diamino platinum complexes. The antitumor activity of these compounds is reported.

  使用D-甘露醇的立体控制性羟基操纵合成了与顺式铂相关的非环临近多元醇配合物。通过对3,4-二偶氮基己醇的控制性断裂，得到了相应的D-三赤醇和D-木糖醇类似物，这些类似物被转化为它们的二氨基铂配合物。报道了这些化合物的抗肿瘤活性。
• Alkylating Agents Related to 2,2′-Biaziridine. II.¹ N,N′-Dicarbethoxy-2,2′-biaziridine
  作者：Peter W. Feit、Ole Tvaermose. Nielsen

  DOI：10.1021/jm00317a039

  日期：1967.9
• Cyclic Disulfide C(8) Iminoporfiromycin:  Nucleophilic Activation of a Porfiromycin
  作者：Sang Hyup Lee、Harold Kohn

  DOI：10.1021/ja030577r

  日期：2004.4.1

  The clinical success of mitomycin C (1) and its associated toxicities and resistance have led to efforts to prepare semisynthetic analogues (i.e., KW-2149 (3), BMS-181174 (4)) that have improved pharmacological profiles. In this study, we report the preparation and evaluation of the novel 7-N-(1'-amino-4',5'-dithian-2'-yl)porfiromycin C(8) cyclized imine (6) and its reference compound, 7-N-(1'-aminocyclohex-2'-yl)porfiromycin C(8) cyclized imine (13). Porfiromycin 6 contains a disulfide unit that, upon cleavage, may provide thiol(s) that affect drug reactivity. We demonstrated that phosphines dramatically accelerated 6 activation and solvolysis in methanolic solutions ("pH 7.4") compared with 13. Porfiromycins 6 and 13 efficiently cross-linked EcoRI-linearized pBR322 DNA upon addition of Et3P. We found enhanced levels of interstrand cross-link (ISC) adducts for 6 and 13 compared with porfiromycin (7) and that 6 was more efficient than 13. The large Et3P-mediated rate enhancements for the solvolysis of 6 compared with 13 and a N(7)-substituted analogue of 1, and the increased levels of ISC adducts for 6 compared with 13 and 7 are attributed to a nucleophile-assisted disulfide cleavage process that permits porfiromycin activation and nucleophile (MeOH, DNA) adduction. The in vitro antiproliferative activities of 6 and 13 using the A549 tumor cell line (lung adenocarcinoma) were determined under aerobic and hypoxic conditions and then compared with 7. Both 6 and 13 were more cytotoxic than 7, with 13 being more potent than 6. The C(8) iminoporfiromycins 6 and 13 displayed anticancer profiles similar to 3.