Diethyl N-(ethylsulfanyl)hydrazodicarboxylate | 232589-55-8

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫基化合物
• 英文名称: Diethyl N-(ethylsulfanyl)hydrazodicarboxylate
• 英文别名: diethyl N-ethylsulfenylhydrazodicarboxylate；ethyl N-(ethoxycarbonylamino)-N-ethylsulfanylcarbamate
• CAS: 232589-55-8
• 化学式: C₈H₁₆N₂O₄S
• 分子量: 236.292
• InChiKey: HTKAMPMCTURUFU-UHFFFAOYSA-N

物化性质

• 密度：
  1.195±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  93.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-硫代-b-D-葡萄糖四乙酸酯 、 Diethyl N-(ethylsulfanyl)hydrazodicarboxylate 以 二氯甲烷 为溶剂， 反应 0.08h， 以100%的产率得到ethyl (2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl) disulfide
  参考文献：
  名称：

  Solid-Phase Synthesis of Thio-oligosaccharides

  摘要：

  No protecting groups are present in the highly reactive polymer-bound sugar 1-thiolates 1, which undergo reactions with sugar triflates 2 to give thio-oligosaccharides 3 in high yield. Tr=trityl=triphenylmethyl, Tf=trifluoromethylsulfonyl, Bz=benzoyl.

  DOI：

  10.1002/(sici)1521-3773(19990614)38:12<1782::aid-anie1782>3.0.co;2-1
• 作为产物：
  描述：

  乙硫醇 、 偶氮二甲酸二乙酯 以 苯 为溶剂， 反应 2.0h， 生成 Diethyl N-(ethylsulfanyl)hydrazodicarboxylate
  参考文献：
  名称：

  Design and Synthesis of Sulfur Based Inhibitors of Matrix Metalloproteinase-1.

  摘要：

  成纤维细胞胶原酶（MMP-1）是基质金属蛋白酶家族的一员，被认为是关节炎的病理机制之一，它通过切割软骨中的三重螺旋II型胶原蛋白发挥作用。基于其活性位点锌结合模式与羟肟酸的相似性，我们设计并合成了含有α-巯基羰基的化合物（3—5），这些化合物包含了作为酶识别位点的不同肽序列。包含P4–P1肽的化合物（3）表现出与羟肟酸（1）和羧酸（2）类型抑制剂相当的强抑制作用，对MMP-1的IC50值为10−6小于M的量级。然而，与抑制剂（3）相关的化合物（6—8）显示出下降或无抑制活性。这些结果表明，羰基和巯基的共存可能对抑制作用至关重要，并且这两个官能团之间的距离对抑制效能也很重要。对于Pn'肽的包含化合物（4a—k），除了4h和4k以外，所有化合物的IC50值均低于亚纳摩尔。其中，在强抑制作用方面，Leu作为P1'氨基酸优于Phe和Val，而P2'位的氨基酸是必要的，并且优先选择Phe。将Pn肽插入4d或4k生成化合物5a—c，并未增加4d和4k的活性。将巯基替换为其他官能团则失去了化合物4a的活性。通过合成4a的两种异构体还确定了在巯基连接位置的立体化学偏好，发现S构型的化合物（36b）的效能约为相应R-异构体（36a）的100倍。

  DOI：

  10.1248/cpb.50.239

文献信息

• Design and Synthesis of Sulfur Based Inhibitors of Matrix Metalloproteinase-1.
  作者：Tetsunori Fujisawa、Shinjiro Odake、Yuji Ogawa、Junko Yasuda、Yasuo Morita、Tadanori Morikawa

  DOI：10.1248/cpb.50.239

  日期：——

  Fibroblast collagenase (MMP-1), a member of the matrix metalloproteinases family, is believed to be a pathogenesis of arthritis, by cleaving triple-helical type II collagen in cartilage. From the similarity of the active site zinc binding mode with hydroxamate, we designed and synthesized α-mercaptocarbonyl possessing compounds (3—5), which incorporated various peptide sequences as enzyme recognition sites. The P4–P1 peptide incorporating compound (3) exhibited as potent inhibition as the hydroxamate (1) and the carboxylate (2) type inhibitors, with an IC50 of 10−6 M order against MMP-1. But the inhibitor (3) related compounds (6—8) displayed decreased or no inhibitory potencies. These results suggest that the existence of both the carbonyl and thiol groups might be critical for the inhibition, and the distance between the two functional groups is important for inhibitory potency. For Pn′ peptide incorporating compounds (4a—k), except for 4h and 4k, all compounds showed IC50 values under sub-nanomolar. Among them, for potent inhibition, Leu was better than Phe and Val as the P1′ amino acid, and the P2′ position amino acid was necessary, and preferentially Phe. Insertion of the Pn peptide into 4d or 4k, giving compounds 5a—c, did not increase the activities of 4d and 4k. Substitution of the mercapto group with other functional groups lost the activity of compound 4a. The stereochemical preference at the thiol-attached position was also determined by preparation of both isomers of 4a. It was found that the S configuration compound (36b) is approximately 100 times more potent than the corresponding R-isomer (36a).

  成纤维细胞胶原酶（MMP-1）是基质金属蛋白酶家族的一员，被认为是关节炎的病理机制之一，它通过切割软骨中的三重螺旋II型胶原蛋白发挥作用。基于其活性位点锌结合模式与羟肟酸的相似性，我们设计并合成了含有α-巯基羰基的化合物（3—5），这些化合物包含了作为酶识别位点的不同肽序列。包含P4–P1肽的化合物（3）表现出与羟肟酸（1）和羧酸（2）类型抑制剂相当的强抑制作用，对MMP-1的IC50值为10−6小于M的量级。然而，与抑制剂（3）相关的化合物（6—8）显示出下降或无抑制活性。这些结果表明，羰基和巯基的共存可能对抑制作用至关重要，并且这两个官能团之间的距离对抑制效能也很重要。对于Pn'肽的包含化合物（4a—k），除了4h和4k以外，所有化合物的IC50值均低于亚纳摩尔。其中，在强抑制作用方面，Leu作为P1'氨基酸优于Phe和Val，而P2'位的氨基酸是必要的，并且优先选择Phe。将Pn肽插入4d或4k生成化合物5a—c，并未增加4d和4k的活性。将巯基替换为其他官能团则失去了化合物4a的活性。通过合成4a的两种异构体还确定了在巯基连接位置的立体化学偏好，发现S构型的化合物（36b）的效能约为相应R-异构体（36a）的100倍。
• Focused acoustic energy in the preparation and screening of combinatorial libraries
  申请人：——

  公开号：US20020061258A1

  公开（公告）日：2002-05-23

  The present invention provides a method for the acoustic ejection of fluid droplets from each of a plurality of fluid-containing reservoirs to prepare combinatorial libraries in the form of microarrays. An acoustic ejection device is used comprised of a plurality of fluid reservoirs, an ejector for generating acoustic radiation and the acoustic radiation at a focal point near the fluid surface in each of the reservoirs, and a means for positioning the ejector in acoustically coupled relationship to each of the reservoirs. The combinatorial libraries may comprise biological or nonbiological moieties.

  本发明提供了一种从多个含流体贮液器中的每个贮液器中以声波喷射流体液滴的方法，以制备微阵列形式的组合文库。使用的声学喷射装置包括多个流体贮槽、用于产生声辐射的喷射器和在每个贮槽中流体表面附近的焦点处的声辐射，以及将喷射器定位在与每个贮槽有声学耦合关系的位置的装置。组合库可以包括生物或非生物分子。
• High-throughput biomolecular crystallization and biomolecular crystal screening
  申请人：——

  公开号：US20030048341A1

  公开（公告）日：2003-03-13

  The present invention provides a method for the acoustic ejection of fluid droplets from fluid-containing reservoirs to form small volumes high throughput combinatorial experimentation for crystallization. The method is especially suited to preparing combinatorial libraries of small volume crystallization experiments for crystallizing difficult to crystallize biomacromolecules. The small volumes conserve costly and difficult to obtain macromolecules and permit an increased number of experimental crystallization conditions tested for an amount of the biomacromolecule of interest for crystallization. The time required for the experiments is greatly reduced by the scaled down experimental volumes. The invention is conducive to forming high density microarrays of small volume crystallization experiments. Acoustic detection of crystals in situ and distinction between biomacromolecular and non-biomacromolecular crystals is also taught.

  本发明提供了一种从含流体的储液器中以声学方式喷射流体液滴以形成小体积高通量结晶组合实验的方法。该方法特别适用于制备小体积结晶实验组合库，用于结晶难以结晶的生物大分子。小体积结晶节省了昂贵且难以获得的大分子，并允许对一定量的感兴趣的生物大分子进行更多的结晶实验条件测试。由于实验体积缩小，实验所需时间大大缩短。本发明有利于形成小体积结晶实验的高密度微阵列。本发明还可对晶体进行原位声学检测，并区分生物大分子和非生物大分子晶体。
• 1-GALACTOSE DERIVATIVES
  申请人：SYNSORB Biotech Inc.

  公开号：EP0937093A2

  公开（公告）日：1999-08-25
• SACCHARIDE DERIVATIVES
  申请人：SYNSORB Biotech Inc.

  公开号：EP0939759A2

  公开（公告）日：1999-09-08