N-(9H-fluoren-9-ylmethoxycarbonyl)-6-aminohexanoic acid chloride | 936333-52-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: N-(9H-fluoren-9-ylmethoxycarbonyl)-6-aminohexanoic acid chloride
• 英文别名: 9H-fluoren-9-ylmethyl N-(6-chloro-6-oxohexyl)carbamate
• CAS: 936333-52-7
• 化学式: C₂₁H₂₂ClNO₃
• 分子量: 371.864
• InChiKey: KOESUXCCGWWECN-UHFFFAOYSA-N

物化性质

• 沸点：
  544.2±33.0 °C(Predicted)
• 密度：
  1.216±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(9H-fluoren-9-ylmethoxycarbonyl)-6-aminohexanoic acid chloride 在 哌啶 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 N-(2-amino-4-fluorophenyl)-6-[(2-morpholin-4-ylacetyl)amino]hexanamide
  参考文献：
  名称：

  Compositions Including 6-Aminohexanoic Acid Derivatives As HDAC Inhibitors

  摘要：

  这项发明涉及到式（I）中的化合物，其中Cy1、L1、Y、R1、L2和Ar2的定义如下，用于治疗癌症、炎症性疾病和神经系统疾病。

  公开号：

  US20120094971A1
• 作为产物：
  描述：

  芴甲氧羰酰基-6-氨基己酸 在 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以91%的产率得到N-(9H-fluoren-9-ylmethoxycarbonyl)-6-aminohexanoic acid chloride
  参考文献：
  名称：

  Rapid and controllable covalent functionalization of single-walled carbon nanotubes at room temperature

  摘要：

  我们报告了一种快速高效的程序，用于功能化单壁碳纳米管（SWNT），其中通过还原SWNT与二酰过氧化物衍生物之间的氧化还原反应在室温下生成的自由基被共价连接到SWNT壁上。

  DOI：

  10.1039/b712299c

文献信息

• New Nonnucleoside Substrates for Terminal Deoxynucleotidyl Transferase: Synthesis and Dependence of Substrate Properties on Structure
  作者：A. L. Khandazhinskaya、M. K. Kukhanova、M. V. Jasko

  DOI：10.1007/s11171-005-0048-y

  日期：2005.7

  N-(9-Fluorenylmethoxycarbonyl)-ω-aminoalkyl-, N-(9-fluorenylmethoxycarbonyl)-8-amino-3,6-dioxaoctyl, and N-[(9-fluorenylmethoxycarbonyl)-6-aminohexanoyl]-2-aminoethyl triphosphates were synthesized. All of them were shown to be the substrates of the calf thymus terminal deoxynucleotidyl transferase. Their substrate properties depend on the length and structure of the linker between the 9-fluorenylmethoxycarbonyl and triphosphate moieties.

  合成了三种化合物：N-(9-芴甲氧羰基)-ω-氨基烷基-, N-(9-芴甲氧羰基)-8-氨基-3,6-二氧杂辛基-, 和 N-[(9-芴甲氧羰基)-6-氨基己酰基]-2-氨基乙基三磷酸盐。所有这些化合物都被证明是牛胸腺末端脱氧核苷酸转移酶的底物。它们的底物性质取决于连接9-芴甲氧羰基和三磷酸基团之间链的长度和结构。
• [EN] ANTIFOLATE LINKER-DRUGS AND ANTIBODY-DRUG CONJUGATES<br/>[FR] MÉDICAMENTS LIEURS D'ANTIFOLATE ET CONJUGUÉS ANTICORPS-MÉDICAMENT
  申请人：BYONDIS BV

  公开号：WO2022008419A1

  公开（公告）日：2022-01-13

  The present invention relates to novel antifolate linker-drugs, conjugates comprising such antifolate linker-drugs, and the use thereof in the treatment of diseases, such as cancer, autoimmune and infectious diseases, optionally in combination with other therapeutic agents.

  本发明涉及新型抗叶酸连接剂药物，包括这种抗叶酸连接剂的共轭物，并将其用于治疗疾病，如癌症、自身免疫和传染病，可选择性地与其他治疗剂联合使用。
• COMPOUNDS
  申请人：Woscholski Rudiger

  公开号：US20090221702A1

  公开（公告）日：2009-09-03

  The present invention provides the use of a compound of the Formula: (I) wherein R 1 is C 1-5 alkoxy, OCOC 1-3 Alkyl, O(CH 2 ) 2 O(CH 2 ) 2 O(CH 2 ) 2 OMe, O(CH 2 ) 2 O(CH 2 ) 2 O(CH 2 ) 2 OH or OH; R 2 is H, (CH 2 ) n OH, OCH 3 , Hal or (II) or (III) R 3 is H or (CH 2 ) n OH; and R 4 is C 1-6 alkyl, optionally substituted by one or more of Hal, OH, COCH 3 , NH 2 , NHCH 3 , NHMe, NMe 2 , OCOCH 3 , CO 2 H or esters or amides thereof where n is 1-5; and pharmaceutically acceptable salts thereof, in the manufacture of a medicament for use in modulating PKB activity.

  本发明提供了一种使用以下化合物的方法：其中R1是C1-5烷氧基，OCOC1-3烷基，O(CH2)2O( )2O( )2OMe，O( )2O( )2O( )2OH或OH；R2是H，( )nOH，OCH3，卤素或(II)或(III)；R3是H或( )nOH；R4是C1-6烷基，可选择地被一个或多个卤素、OH、COCH3、NH2、NHCH3、NHMe、NMe2、OCOCH3、CO2H或其酯或酰胺所取代，其中n为1-5；以及其在制备用于调节PKB活性的药物中的药用盐。
• COMPOSITIONS INCLUDING 6-AMINOHEXANOIC ACID DERIVATIVES AS HDAC INHIBITORS
  申请人：BIOMARIN PHARMACEUTICAL INC.

  公开号：US20160122290A1

  公开（公告）日：2016-05-05

  This invention relates to compounds of Formula (I) wherein Cy 1 , L 1 , Y, R 1 , L 2 , and Ar2 are defined herein, for the treatment of cancers, inflammatory disorders, and neurological conditions.

  本发明涉及式（I）的化合物，其中Cy1，L1，Y，R1，L2和Ar2在此定义，用于治疗癌症，炎症性疾病和神经系统疾病。
• Guanidinium-Functionalized Flexible Azaproline Transporter for Efficient Intracellular Delivery of Proapoptotic Peptide and PDL1 Antisense Morpholino Oligo in Human Carcinoma Cells <i>In Vitro</i>
  作者：Abhishek Gupta、Shalini Gupta、Ujjal Das、Surajit Sinha

  DOI：10.1021/acs.bioconjchem.2c00129

  日期：2022.5.18

  Cell-penetrating peptides (CPPs) are structurally diverse sophisticated tools endowed with high arginine content, amphipathicity, and well-adopted suitable secondary structures. Despite its capability of breaching the lipid barriers, CPP has major limitations such as in vivo metabolic instability, poor bioavailability, and reduced endosomal escape tendency, which are yet to be improved. In this context, we first have introduced a new class of cellular transporter having a guanidinium-functionalized δ-azaproline (δ-azp)-containing peptide where the δ-azp structurally resembles the “proline” amino acid having an additional “N” at the δ-position. This non-natural peptidic backbone was found to impart proteolytic stability, as reported earlier by our group. Herein, we report the synthesis of a flexible azaproline-tetraguanidinium transporter named FAT along with a revised scalable methodology for δ-azp compared to our previously reported procedure. FAT shows a random-coil-like structure as determined by CD spectroscopy, and is hence structurally different from the polyproline PPII helix. Direct translocation is predicted to be the possible mode of the cellular entrance of FAT into CHO cells when the “Bodipy” fluorophore is covalently attached as the cargo. Simultaneously, two other macromolecular therapeutics, e.g., proapoptotic domain peptide (PAD, a 14-mer peptide) and programmed death ligand 1 (PDL1) morpholino (a 25-mer antisense oligo), were successfully conjugated with FAT and delivered into human carcinoma cells, and their efficacy was analyzed by MTT assay and western blot technique, respectively. Having obtained promising results in internalizing different types of cargos, FAT could be envisaged as a potential drug delivery agent as an alternative to natural CPPs for future application.

  细胞渗透肽（CPP）是一种结构多样、功能复杂的工具，具有高精氨酸含量、两亲性和良好的次级结构。尽管CPP能够突破脂质屏障，但它存在一些重大局限性，例如体内代谢不稳定、生物利用度低和内体逃逸倾向降低，这些还有待改进。在这种情况下，我们首先引入了一种新型细胞转运蛋白，它具有一个含胍基的δ-氮杂脯氨酸（δ-azp）肽，其中δ-azp在结构上类似于“脯氨酸”氨基酸，在δ位上有一个额外的“N”。正如我们小组之前报道的那样，这种非天然肽基质具有蛋白水解稳定性。在此，我们报道了一种名为FAT的柔性氮杂脯氨酸-四胍转运蛋白的合成，以及与之前报道的方法相比，一种经过修订的δ-azp可扩展方法。通过CD光谱测定，FAT显示出随机卷曲状结构，因此与聚脯氨酸PPII螺旋结构不同。当“Bodipy”荧光团作为货物共价结合时，预计直接转运是FAT进入CHO细胞的可能模式。同时，其他两种大分子治疗剂，例如促凋亡域肽（PAD，一种14肽）和程序性死亡配体1（PDL1）吗啉（一种25�