ferrocenoyl hydroxybenzotriazole ester | 189116-51-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并三唑类
• 英文名称: ferrocenoyl hydroxybenzotriazole ester
• 英文别名: ferrocenoylbenzotriazole ester；ferrocenyl benzotriazole ester；ferrocenyl benzotriazolate；Fc-COOBt；FcCOOBt；benzotriazol-1-yl cyclopenta-2,4-diene-1-carboxylate;cyclopenta-1,3-diene;iron(2+)
• CAS: 189116-51-6
• 化学式: C₁₇H₁₃FeN₃O₂
• 分子量: 347.156
• InChiKey: AURDPMAYQUCALS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
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• 重原子数：
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• 可旋转键数：
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• 环数：
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• sp3杂化的碳原子比例：
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• 拓扑面积：
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• 氢给体数：
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• 氢受体数：
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反应信息

• 作为反应物：
  描述：

  咪唑 、 ferrocenoyl hydroxybenzotriazole ester 在 Et₃N 作用下， 以 二氯甲烷 为溶剂， 以66%的产率得到1-ferrocenoyl-1H-imidazole
  参考文献：
  名称：

  Ferrocene-histidine conjugates: N-ferrocenoyl-histidyl(imN-ferrocenoyl)methylester: synthesis and structure

  摘要：

  The preparation of the new ferrocenoyl histidyl conjugates N-Fc-His-OMe (2) and N-Fc-His(epsilon-N-Fc)-OMe (3) and of a simple ferrocenoyl imidazole conjugate Fc-Im (4) is reported together with their spectroscopic and electrochemical characterization. The electrochemistry of 3 exhibits two fully reversible one-electron. oxidations, which are due to the stepwise oxidation of the two ferrocenoyl groups. The crystal structure of 3 shows the difference in the chemical environment of the two Fc groups, one being attached to the alpha-N and one being attached to the epsilon-N of the imidazole of histidine. There is no discernible intermolecular interaction present in the crystal structure. (C) 2003 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-328x(03)00182-7
• 作为产物：
  描述：

  二茂铁甲酸 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 ferrocenoyl hydroxybenzotriazole ester
  参考文献：
  名称：

  通过二茂铁扫描探索合成抗菌肽 (synAMPs) 的构效关系

  摘要：

  合成抗菌肽 (SynAMP) 是一类有趣的新型抗生素，用于对抗由耐药菌株引起的感染。在此，我们报告了适用于标准 Fmoc/tBu 固相肽合成的含二茂铁赖氨酸 (FcLys) 的合成。已经合成了一个基于 (Arg-Trp)3 的抗菌肽库，其中所有色氨酸残基都被 FcLys 系统地替换，并评估了它们的生物活性。我们称这种技术为“二茂铁扫描”，类似于用于研究肽中关键相互作用的成熟“丙氨酸扫描”。与不含金属的亲本肽相比，FcLys 肽对革兰氏阳性细菌菌株显示出优异的活性，包括对耐药菌株 MRSA 的活性增加了四倍。此外，与亲本肽相比，该二茂铁酰肽家族的一些成员还显示出高达 16 倍的活性，以对抗革兰氏阴性细菌鲍曼不动杆菌。这种行为将这些 SynAMP 与先前研究的 N 末端二茂铁酰化肽区分开来，后者通常对革兰氏阴性菌的活性显着降低。FcLys 肽还显示出对红细胞 (RBC) 的低溶血活性，这表明其

  DOI：

  10.1002/ejic.201600799

文献信息

• 二茂铁衍生物、其制备方法及用途
  申请人：中国科学院福建物质结构研究所

  公开号：CN103319543B

  公开（公告）日：2018-05-11

  本发明公开式I所示的二茂铁衍生物I其中：R选自:,,,,，等杂环。以式1所示的二茂铁衍生物作为均相媒介或以式1所示的二茂铁衍生物修饰的玻碳电极对半胱氨酸具有显著的电催化氧化特性。以其作为电化学传感器用于检测半胱氨酸、活性生物分子及药物小分子的含量的用途。
• Multielectron Storage and Photo‐Induced Electron Transfer in Oligonuclear Complexes Containing Ruthenium( <scp>II</scp> ) Terpyridine and Ferrocene Building Blocks
  作者：Katja Heinze、Klaus Hempel、Manuela Beckmann

  DOI：10.1002/ejic.200501078

  日期：2006.5

  The heteroleptic complex [(HOOC-tpy)Ru(tpy-NH2)](PF6)2 (tpy = 2,2′;6′,2″-terpyridine) has been incorporated into a multicomponent system with ferrocene moieties attached on either the N-terminal end or the C-terminal end and on both ends of the ruthenium complex. Electrochemical studies reveal almost noninteracting subunits in the oligonuclear systems, whereas ground-state and excited-state optical

  杂配复合物 [(HOOC-tpy)Ru(tpy-NH2)](PF6)2 (tpy = 2,2';6',2"-terpyridine) 已被整合到一个多组分系统中，二茂铁部分连接在N-末端或C-末端和钌络合物的两端。电化学研究揭示了寡核系统中几乎不相互作用的亚基，而基态和激发态的光学性质显示强烈依赖于二茂铁连接的位点。DFT 计算支持对实验结果的解释。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)
• Synthesis, Structure, and Biological Activity of Ferrocenyl Carbohydrate Conjugates
  作者：Cara L. Ferreira、Charles B. Ewart、Cheri A. Barta、Susan Little、Vanessa Yardley、Candice Martins、Elena Polishchuk、Peter J. Smith、John R. Moss、Michael Merkel、Michael J. Adam、Chris Orvig

  DOI：10.1021/ic061166p

  日期：2006.10.1

  (12) was synthesized via amide coupling of an activated ferrocenyl ester with the corresponding carbohydrate. All compounds were characterized by elemental analysis, 1H NMR spectroscopy, and mass spectrometry. X-ray crystallography confirmed the solid-state structure of three ferrocenyl carbohydrate conjugates: 2-N-(1,3,4,6-tetra-O-acetyl-2-amino-2-deoxy-D-glucopyranose)-1-ferrocene carboxamide (1), 1-S-(2

  合成了七个二茂铁基碳水化合物缀合物。单糖衍生物与二茂铁碳酰氯的偶联反应产生了6-N-（甲基2,3,4-三-O-乙酰基-6-氨基-6-脱氧-α-D-吡喃葡萄糖苷）}-1-二茂铁羧酰胺（ 3），1-O-（2,3,4,6-四-O-苄基-D-吡喃葡萄糖）}-1-二茂铁羧酸盐（4）和6-O-（1,2,3， （4-四-O-乙酰基-β-D-吡喃葡萄糖）}-1-二茂铁羧酸盐（5）。类似地，将1，1'-双（羰基氯）二茂铁与适当的糖偶联以产生双取代的类似物bis 6-N-（甲基2,3,4-三-O-乙酰基-6-氨基-6-脱氧-α-D-吡喃葡萄糖苷）}-1,1'-二茂铁羧酰胺（8），双1-O-（2,3,4,6-四-O-苄基-D-吡喃葡萄糖）}-1， 1'-二茂铁羧酸盐（9）和双6-O-（1,2,3,4-四-O-乙酰基-β-D-吡喃葡萄糖）}-1,1'-二茂铁羧酸盐（10）。通过活化的二茂铁基酯与相应的
• Ferrocene tripeptide Gly-Pro-Arg conjugates: Synthesis and inhibitory effects on Alzheimer’s Aβ1–42 fibrillogenesis and Aβ-induced cytotoxicity in vitro
  作者：Binbin Zhou、Chun-Lan Li、Yuan-Qiang Hao、Muya Chabu Johnny、You-Nian Liu、Juan Li

  DOI：10.1016/j.bmc.2012.11.030

  日期：2013.1

  Alzheimer's disease (AD) is the most common cause of dementia, and currently there is no clinical treatment to cure it or to halt its progression. Aggregation and fibril formation of beta-amyloid peptides (A beta) are central events in the pathogenesis of AD. Many efforts have been spent on the development of effective inhibitors to prevent A beta fibrillogenesis and cause disaggregation of preformed A beta fibrils. In this study, the conjugates of ferrocene and Gly-Pro-Arg (GPR) tripeptide, Boc-Gly-Pro-Arg(NO2)-Fca-OMe (4, GPR-Fca) and Fc-Gly-Pro-Arg-OMe (7, Fc-GPR) (Fc: ferrocene; Fca: ferrocene amino acid) were synthesized by HOBT/HBTU protocol in solution. These ferrocene GPR conjugates were employed to inhibit A beta(1-42) fibrillogenesis and to disaggregate preformed A beta fibrils. The inhibitory properties of ferrocene GPR conjugates on A beta(1-42) fibrillogenesis were evaluated by thioflavin T (ThT) fluorescence assay, and confirmed by atomic force microscopy (AFM) analysis. The interaction between the ferrocene GPR conjugates and A beta(1-42) was monitored by electrochemical means. Our results showed that both GPR and GPR-Fca can significantly inhibit the fibril formation of A beta(1-42), and cause disaggregation of the preformed fibrils. As expected, GPR-Fca shows stronger inhibitory effect on A beta(1-42) fibrillogenesis than that of its parent peptide GPR. In contrast, Fc-GPR shows no inhibitory effect on fibrillogenesis of A beta(1-42). Furthermore, GPR-Fca demonstrates significantly protection against A beta-induced cytotoxicity and exhibits high resistance to proteolysis and good lipophilicity. (C) 2012 Elsevier Ltd. All rights reserved.
• Ferrocenoyl Amino Acids:  A Synthetic and Structural Study
  作者：Heinz-Bernhard Kraatz、Janusz Lusztyk、Gary D. Enright

  DOI：10.1021/ic961454t

  日期：1997.5.1

  A series of ester-protected amino acids were coupled to ferrocenecarboxylic acid (1) using the DCC/HOBt protocol to give ferrocenoyl N-amino acids (amino acid = Glu(OBz)(2) (2a), Gly(OEt) (2b), Pro(OBz) (2c), Cys(SBz)OMe (2d), Ala(OBz) (2e), Tyr(OBz) (2f), Phe(OBz) (2g)). All products were fully characterized. The intermediate hydroxybenzotriazole active ester FcCOOBt (3) was isolated and fully characterized. The solid state structures of 2a, 2d, and 3 were determined by single-crystal X-ray diffraction. 2a: monoclinic P2(1) with a = 11.8142(5) Angstrom, b = 9.7560(5) Angstrom, c = 22.9456(10) Angstrom, beta = 90.246(5)degrees, V = 2644.7(2) Angstrom(3), Z = 2, R = 0.046. 2d: orthorhombic P2(1)2(1)2(1) with a = 9.957(2) Angstrom, b = 11.680(2) Angstrom, c = 36.452(2) Angstrom, V = 4239.5(13) Angstrom(3), Z = 4, R = 0.065. The solid state structures of 2a and 2d show extensive C=O ... H-N hydrogen bonding. 3: triclinic with a 7.0391(5) Angstrom, b = 10.7922(7) Angstrom, c = 11.1690(7) Angstrom, alpha = 108.071(5)degrees, beta = 107.957(5)degrees, gamma = 103.896(5)degrees, V = 712.5(2) Angstrom(3), Z = 2, R = 0.030. The long ester bond distance of 1.427(2) Angstrom provides a rationale for its inherent reactivity toward primary and secondary amines.