benzyl (6-hydroxyhexylcarbamoyl)methylcarbamate | 75937-30-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: benzyl (6-hydroxyhexylcarbamoyl)methylcarbamate
• 英文别名: Benzyl (2-((6-hydroxyhexyl)amino)-2-oxoethyl)carbamate；benzyl N-[2-(6-hydroxyhexylamino)-2-oxoethyl]carbamate
• CAS: 75937-30-3
• 化学式: C₁₆H₂₄N₂O₄
• 分子量: 308.378
• InChiKey: VSEKUOVFAUMMKE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  22
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  87.7
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  benzyl (6-hydroxyhexylcarbamoyl)methylcarbamate 在 palladium on activated charcoal 氨 、 氢气 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 生成 1-β-[6-((R)-alanylglycylamino)hex-1-yl]-β-L-fucopyranose
  参考文献：
  名称：

  Synthesis and Activity of Dipeptides, Linked to Targeting Ligands, as Specific NK Cell Enhancers

  摘要：

  Water soluble analogues of the lipophilic immunostimulant, octadecyl D-alanyl-L-glutamine, BCH-527, were synthesized and evaluated for the ability to stimulate natural killer (NK) cells. One of these compounds in which the octadecyl chain of BCH-527 was replaced with a shorter chain alcohol, 6-(D-alanyl-L-glutaminylamino)hexan-1-ol, 9, displayed an in vitro stimulation of NK cells comparable to that of interleukin 2 (IL 2). However, when the hydroxyl of 9 was linked to L-fucose to yield 1-beta-[6-(D-alanyl-L-glutaminylamino)hex-1-yl]-L-fucopyranose (BCH-2537 1), the observed stimulation of NK cells was greater than that observed with IL 2. Further evaluation of these compounds revealed that the improved in vitro activity of BCH-2537 was more pronounced in vivo. That is, while both compounds significantly increased splenic NK cells, only BCH-2537 significantly increased the activity of these cells in vivo. In terms of a structure-activity relationship, NK cell activity was sensitive to minor structural modifications. It was influenced by conservative substitutions within the dipeptide, the length of the hydrocarbon chain, and the functionality at the end of the chain. No other compound enhanced NK cell activity to the extent exhibited by BCH-2537, although a few were equipotent to 9.

  DOI：

  10.1021/jm970734v
• 作为产物：
  描述：

  6-氨基-1-己醇 、 N-苄氧羰基甘氨酸 在 N-羟基丁二酰亚胺 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 以45%的产率得到benzyl (6-hydroxyhexylcarbamoyl)methylcarbamate
  参考文献：
  名称：

  SYNTHESIS METHOD OF GLYCO-DRUG RADIOTRACER PRECURSOR

  摘要：

  揭示了一种新的糖基药物放射性示踪剂前体的合成方法。完成主要结构Z-Gly-ah的合成后，加入甘露胺GalNAc(OAc)4进行偶联反应。然后直接从二氯甲烷中分离产物。因此，液相色谱提取过程中甘露胺的损失得到了减少。此外，保护基使用碳苯氧基（简称Cbz或Z）以确保相位的一致性，而不是三氟乙酰基。成本和合成时间也大大降低。

  公开号：

  US20140066609A1

文献信息

• METHOD FOR PREPARING PRECURSOR USED FOR LABELING HEPATOCYTE RECEPTOR AND CONTAINING TRISACCHARIDE AND DTPA LIGAND
  申请人：LIN CHIH-YUAN

  公开号：US20140046045A1

  公开（公告）日：2014-02-13

  A method for preparing a precursor used to label hepatocyte receptors is revealed. The precursor contains a bifunctional structure including trisaccharide and DTPA ligand. During synthesis processes of the precursor, silica gel columns and Reverse phase-18 (RP-18) columns are used for purification. Thus both the purification times and cost of each purification are reduced. Moreover, use diethyl ether to facilitate precipitation of products and remove a part of coupling reagent. Removing the coupling reagent helps purification of products. Furthermore, N α ,N α -bis(carboxymethyl)-L-lysine hydrate and benzyl chloroformate are coupled to form a trisaccharide skeleton so as to ensure the yield rate of trisaccharide structure.

  揭示了一种用于标记肝细胞受体的前体制备方法。该前体包含一个双功能结构，包括三糖和DTPA配体。在前体的合成过程中，使用硅胶柱和反相-18（RP-18）柱进行纯化。因此，每次纯化的纯化次数和成本都得到了降低。此外，使用乙醚有助于沉淀产物并去除部分偶联试剂。去除偶联试剂有助于产物的纯化。此外，Nα，Nα-双（羧甲基）-L-赖氨酸水合物和苄基氯甲酸酯被耦合形成三糖骨架，以确保三糖结构的产率。
• NOVEL GALL BLADDER IMAGING AGENT AND ITS PREPARATION METHOD
  申请人：INSTITUTE OF NUCLEAR ENERGY RESEARCH ATOMIC ENERGY COUNCIL, EXECUTIVE YUAN

  公开号：US20140186262A1

  公开（公告）日：2014-07-03

  A novel gall bladder image agent which includes a radio-labelled MAG3-tri-galactosamine, and its preparation method, which includes reacting mercaptoacetyltriglycine (MAG3)-tri-galactosamine, SnF2 and Tc-99m in the presence of a phosphate buffer solution (at pH of from 10.0˜12.0) to obtain Tc-99m-MAG3-tri-galactosamine, when the MAG3-tri-galactosamine is MAG3-DCM-Lys(Gah-GalNAc)3 (where DCM represents a dicarboxymethyl group, and Gah represents a glycine-aminohexyl group), it obtains a labelling yield of at least 90%, and its specific radioactivity is at least 7.0×109 Bq/mg.

  一种新型的胆囊成像剂，包括放射性标记的MAG3-三半乳糖胺，并且其制备方法包括在磷酸盐缓冲溶液（pH值在10.0~12.0之间）中反应巯基乙酰三甘氨酸（MAG3）-三半乳糖胺、SnF2和Tc-99m，以获得Tc-99m-MAG3-三半乳糖胺，当MAG3-三半乳糖胺是MAG3-DCM-Lys（Gah-GalNAc）3（其中DCM代表二羧甲基基团，Gah代表甘氨酰己基基团）时，获得至少90％的标记收率，其特异性放射性至少为7.0×109 Bq/mg。
• SYNTHESIS METHOD OF GLYCO-DRUG RADIOTRACER PRECURSOR
  申请人：LU Kuei-Lin

  公开号：US20140066609A1

  公开（公告）日：2014-03-06

  A novel synthesis method of Glyco-drug radiotracer precursor is revealed. After completing synthesis of Z-Gly-ah (main structure), galactosamine GalNAc(OAc) 4 is added to have coupling reaction. Then a product is separated directly from dichloromethane. Thus loss of galactosamine during extraction with liquid chromatography is reduced. Moreover, instead of trifluoroacetyl group, carbobenzoxy (abbreviated as Cbz or Z) is used as a protecting group to ensure uniformity of the phase. The cost and synthesis time are also dramatically reduced.

  揭示了一种新的糖基药物放射性示踪剂前体的合成方法。完成主要结构Z-Gly-ah的合成后，加入甘露胺GalNAc(OAc)4进行偶联反应。然后直接从二氯甲烷中分离产物。因此，液相色谱提取过程中甘露胺的损失得到了减少。此外，保护基使用碳苯氧基（简称Cbz或Z）以确保相位的一致性，而不是三氟乙酰基。成本和合成时间也大大降低。
• Ligand analog-irreversible enzyme inhibitor conjugates and methods for
  申请人：Abbott Laboratories

  公开号：US04273866A1

  公开（公告）日：1981-06-16

  The present invention encompasses a method for determining ligands in test samples comprising intermixing with the test sample a ligand analog-irreversible enzyme inhibitor conjugate and a binding protein bindable to the ligand and the ligand analog-irreversible enzyme inhibitor conjugate and wherein the amount of ligand analog-irreversible enzyme inhibitor conjugate bound by the binding protein is related to the amount of ligand in the test sample, said binding protein inactivating the irreversible enzyme inhibitor when bound to the ligand analog portion of the conjugate; intermixing an enzyme which is irreversibly inhibited by the ligand analog-irreversible enzyme inhibitor conjugate unbound by the binding protein; and intermixing substrate to the enzyme and monitoring the enzyme substrate reaction. The invention also includes ligand analog-irreversible enzyme inhibitor conjugates useful as reagents in practicing the method. Methods and reagents of the present are particularly useful in determining drugs, hormones, and the like in biological fluids.

  本发明涵盖了一种测定试样中配体的方法，包括将配体类似物-不可逆酶抑制剂共轭物和可与配体及配体类似物-不可逆酶抑制剂共轭物结合的结合蛋白与试样混合，其中结合蛋白结合的配体类似物-不可逆酶抑制剂共轭物的数量与试样中配体的数量相关，当结合蛋白与共轭物的配体类似物部分结合时，结合蛋白失活不可逆酶抑制剂。将未被结合蛋白结合的配体类似物-不可逆酶抑制剂与酶混合，该酶被配体类似物-不可逆酶抑制剂不可逆抑制，然后将底物混合到酶中并监测酶底物反应。本发明还包括作为试剂在实践该方法中有用的配体类似物-不可逆酶抑制剂共轭物。本发明的方法和试剂在测定生物液中的药物、激素等方面特别有用。
• Ligand analog-irreversible enzyme inhibitor conjugates
  申请人：Abbott Laboratories

  公开号：US04550163A1

  公开（公告）日：1985-10-29

  The present invention encompasses a method for determining ligands in test samples comprising intermixing with the test sample a ligand analog-irreversible enzyme inhibitor conjugate and a binding protein bindable to the ligand and the ligand analog-irreversible enzyme inhibitor conjugate and wherein the amount of ligand analog-irreversible enzyme inhibitor conjugate bound by the binding protein is related to the amount of ligand in the test sample, said binding protein inactivating the irreversible enzyme inhibitor when bound to the ligand analog portion of the conjugate; intermixing an enzyme which is irreversibly inhibited by the ligand analog-irreversible enzyme inhibitor conjugate unbound by the binding protein; and intermixing substrate to the enzyme and monitoring the enzyme substrate reaction. The invention also includes ligand analog-irreversible enzyme inhibitor conjugates useful as reagents in practicing the method. Methods and reagents of the present are particularly useful in determining drugs, hormones, and the like in biological fluids.

  本发明涵盖了一种测定试样中配体的方法，包括将配体类似物-不可逆酶抑制剂共轭物和可结合于配体和配体类似物-不可逆酶抑制剂共轭物的结合蛋白与试样混合，其中结合蛋白结合的配体类似物-不可逆酶抑制剂共轭物的数量与试样中配体的数量相关，所述结合蛋白在结合到共轭物的配体类似物部分时失活不可逆酶抑制剂；混合一种被配体类似物-不可逆酶抑制剂共轭物未结合的不可逆酶抑制的酶；混合底物到酶中，并监测酶底物反应。本发明还包括作为试剂在实践该方法中有用的配体类似物-不可逆酶抑制剂共轭物。本发明的方法和试剂特别适用于测定生物液体中的药物、激素等。