奥吩达唑 | 53733-97-4

• 物质功能分类: 有机原料 - 氨基化合物
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 奥吩达唑
• 中文别名: 奥芬达唑；苄氧羰基-β-丙氨酸-琥珀酰亚胺酯
• 英文名称: N-benzyloxycarbonyl-3-aminopropionic acid succinimide ester
• 英文别名: Cbz-βAla-OSu；Cbz-beta-alanine-N-hydroxysuccinimide ester；Z-β-Ala-OSu；Z-betaAla-OSu；N-Benzyloxycarbonyl-β-alanine N-hydroxysuccinimide ester；N-CBZ-beta-Alanine N-hydroxysuccinimide ester；Z-beta-Ala-osu；(2,5-dioxopyrrolidin-1-yl) 3-(phenylmethoxycarbonylamino)propanoate
• CAS: 53733-97-4
• 化学式: C₁₅H₁₆N₂O₆
• 分子量: 320.302
• InChiKey: XBQSLJICWKEVSC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  6

安全信息

• 海关编码：
  2925190090
• 储存条件：
  -20°C

反应信息

• 作为反应物：
  描述：

  奥吩达唑 在 碳酸氢钠 作用下， 以 乙二醇甲醚 为溶剂， 反应 8.0h， 生成
  参考文献：
  名称：

  Use of adenine nucleotide derivatives to assess the potential of exo-active-site-directed reagents as species- or isozyme-specific enzyme inactivators. 3. Synthesis of adenosine 5'-triphosphate derivatives with N6- or 8-substituents bearing iodoacetyl groups

  摘要：

  Several series of N6- or 8-substituted derivatives of adenosine 5'-triphosphate (ATP) were synthesized. N6-(omega-Aminoalkyl) derivatives of adenosine 5'-monophosphate (AMP) were converted into their omega-N-carbobenzyloxy derivatives, and these were converted, via the 2',3'-O-carbonyl derivatives of their 5'-phosphorimidazolidates, into the corresponding ATP derivatives. Hydrogenolytic removal of the carbobenzyloxy groups, followed by iodoacetylation of the omega-amino groups with N-(iodoacetoxy)succinimide, gave N6-R-ATP, where R = (CH2)nNHCOCH2I (n = 2--8) or (CH2)nCON)CH3)(CH2)mN(CH3)CO(CH2)nNHCOCH2I (n = m = 3; n = 3, m = 4; n = 4, m = 3; n = m = 4). Condensation of N6-(omega-aminoalkyl) derivatives of AMP with N-hydroxysuccinimide esters of omega-[N-(carbobenzyloxy)amino] carboxylic acids gave N6-(CH2)nNHCO(CH2)mNH-Cbz derivatives of AMP which, upon conversion to the corresponding derivatives of ATP, followed by removal of the carbobenzyloxy group and iodoacetylation, as described above, gave N6-(CH2)nNHCO(CH2)mNHCOCH2I-ATP derivatives (n = 3, m = 5 or 6; n = 4, m = 5; n = 6, m = 1--6). The same sequence of reactions starting with N6-[omega-(methylamino)alkyl] derivatives of N6-CH3-AMP gave N6-CH3, N6-(CH2)nH(CH3)CO(CH2)mNHCOCH2I derivatives of ATP (n = 4, m = 3, 5 or 6; n = 6, m = 5 or 6). Reaction of alpha, omega-diaminoalkanes with 8-Br-ATP gave 8-NH(CH2)nNH2 derivatives of ATP, which upon iodoacetylation gave 8-NH(CH2)nNHCOCH2I derivatives of ATP (n = 2, 4, 6, or 8). Substrate and inhibitor properties indicated that the ATP derivatives are potential exco-ATP-site-directed inactivators of hexokinases, adenylate kinases, and pyruvate kinases.

  DOI：

  10.1021/jm00346a009
• 作为产物：
  描述：

  N-羟基丁二酰亚胺 、 N-CBZ-beta-丙氨酸 在 N,N'-二环己基碳二亚胺 作用下， 以 1,4-二氧六环 为溶剂， 生成 奥吩达唑
  参考文献：
  名称：

  桥接异胞嘧啶腺苷化合物：合成和抗菌评估

  摘要：

  在一种新型抗菌剂的方法中，我们合成了一系列5-亚硝基异胞嘧啶，其中6-烷基氨基取代基通过烷基链末端的酰胺键桥接至5'-脱氧腺苷的5'-位部分。还制备了相应的5-硝基类似物系列。没有一种桥接化合物显示出明显的抗菌活性。

  DOI：

  10.1002/jhet.5570230348

文献信息

• An easy preparation of hapten active esters via solid supported EDAC
  作者：Maciej Adamczyk、Jeffrey R. Fishpaugh、Phillip G. Mattingly

  DOI：10.1016/0040-4039(95)01761-6

  日期：1995.11

  Bioconjugates are preferably prepared by reacting an active ester of the hapten of interest to the protein. Preparation of active esters with solid supported EDAC and N-hydroxysuccinunide or pentafluorophenol affords active esters in excellent yield and purity

  生物缀合物优选地通过使感兴趣的半抗原的活性酯与蛋白质反应来制备。用固体负载的EDAC和N-羟基琥珀酰亚胺或五氟苯酚制备活性酯可提供具有优异收率和纯度的活性酯
• Synthesis and kinetic evaluation of S- and N-substituted cysteinylglycines as inhibitors of glyoxalase I
  作者：Philip A. Lyon、Robert Vince

  DOI：10.1021/jm00211a015

  日期：1977.1

  contrast to the previously prepared S-substituted glutathiones, all of the title compounds exhibited noncompetitive inhibition of yeast glyoxalase I. A kinetic evaluation under Yonetani-Thorell conditions established the existence of two binding sites on the glyoxalase I enzyme.

  通过将S-苄基-L-半胱氨酰甘氨酸或S-（对-溴苄基）-L-半胱氨酰甘氨酸与戊二酸酐，琥珀酸酐或适当封闭和活化的氨基酸缩合来制备八个S-和N-取代的L-半胱氨酰甘氨酸。与先前制备的S-取代的谷胱甘肽相反，所有标题化合物均显示出对酵母乙二醛酶I的非竞争性抑制。在Yonetani-Thorell条件下的动力学评估确定了乙二醛酶I酶上存在两个结合位点。
• Inhibitors of Tripeptidyl Peptidase II. 2. Generation of the First Novel Lead Inhibitor of Cholecystokinin-8-Inactivating Peptidase:  A Strategy for the Design of Peptidase Inhibitors
  作者：C. Robin Ganellin、Paul B. Bishop、Ramesh B. Bambal、Suzanne M. T. Chan、James K. Law、Benoit Marabout、Pratibha Mehta Luthra、Andrew N. J. Moore、Olivier Peschard、Pierre Bourgeat、Christiane Rose、Froylan Vargas、Jean-Charles Schwartz

  DOI：10.1021/jm990226g

  日期：2000.2.1

  fluorimetric assay based on the hydrolysis of the artificial substrate Ala-Ala-Phe-amidomethylcoumarin. A series of di- and tripeptides having various alkyl or aryl side chains was studied to determine the accessible volume for binding and to probe the potential for hydrophobic interactions. From this initial study the tripeptides Ile-Pro-Ile-OH (K(i) = 1 microM) and Ala-Pro-Ala-OH (K(i) = 3 microM) and dipeptide

  失活胆囊收缩素8（CCK-8）的肽酶是一种丝氨酸肽酶，已证明是三肽基肽酶II的膜结合同工型（EC 3.4.14.10）。它在Met-Gly键处裂解神经递质CCK-8硫酸盐，得到Asp-Tyr（SO（3）H）-Met-OH + Gly-Trp-Met-Asp-Phe-NH（2）。为了寻找该肽酶的可逆抑制剂，使用基于人工底物Ala-Ala-Phe-酰胺基甲基香豆素水解的荧光分析法来表征酶促结合亚位点。对具有各种烷基或芳基侧链的一系列二肽和三肽进行了研究，以确定可结合的体积并探讨疏水相互作用的可能性。根据这项初步研究，三肽Ile-Pro-Ile-OH（K（i）= 1 microM）和Ala-Pro-Ala-OH（K（i）= 3 microM）和二肽酰胺Val-Nvl-NHBu（K（ i）= 3 microM）作为线索出现。这些结构的比较导致Val-Pro-NHBu（K（i）= 0.57 micr
• Matrix metalloproteinase inhibitors
  申请人：Bristol-Myers Squibb Pharma Company

  公开号：US06656448B1

  公开（公告）日：2003-12-02

  Thus the present invention describes diagnostic agents comprising a diagnostic metal and a compound, wherein the compound comprises: 1-10 targeting moieties;a chelator; and 0-1 linking groups between the targeting moiety and chelator; wherein the targeting moiety is a matrix metalloproteinase inhibitor; and wherein the chelator is capable of conjugating to the diagnostic metal. The present invention also provides novel compositions of the compounds of the invention, kits, and their uses in diagnosis of diseases associated with MMPs.

  因此，本发明描述了包含诊断金属和化合物的诊断试剂，其中该化合物包括：1-10个靶向基团；螯合剂；以及靶向基团和螯合剂之间的0-1个连接基团；其中靶向基团是基质金属蛋白酶抑制剂；螯合剂能够与诊断金属结合。本发明还提供了该化合物的新型组合物、试剂盒以及它们在与基质金属蛋白酶相关的疾病诊断中的用途。
• Fine-Tuning the Balance between Peptide Thioester Cyclization and Racemization
  作者：Stanimir Popovic、Linda Wijsman、Iris R. Landman、Maaike F. Sangster、Dorien Pastoors、Berend B. Veldhorst、Henk Hiemstra、Jan H. van Maarseveen

  DOI：10.1002/ejoc.201501366

  日期：2016.1

  difficult lactamizations are accompanied by side-reactions such as hydrolysis, oligomerization and racemization. By starting from linear peptide 4-methoxythiophenol esters, dilution to 1 mM in combination with phosphate buffer (pH 6.8) intermolecular reactions and racemization could be largely suppressed. Thioesters with the chiral residue at the C-terminus gave the bislactams in yields up to 60% and enantiomeric

  对含有 - 氨基酸和 - 丙氨酸的七元双内酰胺的闭环是有问题的。这种困难的内酰胺化伴随着副反应，例如水解、低聚和外消旋。通过从线性肽 4-甲氧基苯硫酚酯开始，与磷酸盐缓冲液 (pH 6.8) 结合稀释至 1 mM，可以在很大程度上抑制分子间反应和外消旋化。在 C 端具有手性残基的硫酯以高达 60% 的产率和高达 99% 的对映体过量得到双内酰胺。对映体纯双内酰胺仅从 C 端带有丙氨酸的反向序列中获得。