N-(2-(1H-imidazol-4-yl)ethyl)-5-(1,2-dithiolan-3-yl)pentanamide | 214555-09-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二硫杂环戊烷
• 英文名称: N-(2-(1H-imidazol-4-yl)ethyl)-5-(1,2-dithiolan-3-yl)pentanamide
• 英文别名: 5-(1,2-dithiolan-3-yl)-N-[2-(1H-imidazol-5-yl)ethyl]pentanamide；5-(dithiolan-3-yl)-N-[2-(1H-imidazol-5-yl)ethyl]pentanamide
• CAS: 214555-09-6
• 化学式: C₁₃H₂₁N₃OS₂
• 分子量: 299.461
• InChiKey: PVFLLEOWLJKVDE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  108
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  组胺 、 DL-α-硫辛酸-NHS 在 碳酸氢钠 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 以60%的产率得到N-(2-(1H-imidazol-4-yl)ethyl)-5-(1,2-dithiolan-3-yl)pentanamide
  参考文献：
  名称：

  Carbonic Anhydrase Activators: Gold Nanoparticles Coated with Derivatized Histamine, Histidine, and Carnosine Show Enhanced Activatory Effects on Several Mammalian Isoforms

  摘要：

  Lipoic acid moieties were attached to amine or amino acids showing activating properties against the zinc enzyme carbonic anhydrase (CA, EC 4.2.1.1). The obtained lipoic acid conjugates of histamine, L-histidine methyl ester, and L-carnosine methyl ester were attached to gold nanoparticles (NPs) by reaction with Au(III) salts in reducing conditions. The CA activators (CAAs) coated NPs showed low nanomolar activation (K(A)s of 1-9 nM) of relevant cytosolic, membrane-bound, mitochondrial, and transmembrane CA isoforms, such as CA I, II, IV, VA, VII, and XIV. These NPs also effectively activated CAs ex vivo., in whole blood experiments, with an increase of 200-280% of the CA activity. This is the first example of enzyme activation with nanoparticles and may lead to biomedical applications for condition in which the CA activity is diminished, such as aging, Alzheimer's disease, or CA deficiency syndrome.

  DOI：

  10.1021/jm101284a

文献信息

• Dithiolan derivatives, their preparation and their therapeutic effect
  申请人：Sankyo Company Limited

  公开号：EP0869126A1

  公开（公告）日：1998-10-07

  Compounds of formula (I): [in which: one of m and n is 0, and the other is 0, 1 or 2; k is 0 or an integer of from 1 to 12; R1 is hydrogen, one of substituents α, defined below, or an optionally substituted alkyl group; A is a single bond, an oxygen atom, a carbonyl group or a group of formula -N(R2)CO-, -N(R2)CS-, -N(R2)SO2-, -CON(R2)N(R3)CO-, -CON(R2)CO-, -CON(R2)CS-, -CON(R2)SO2-, -O-CO-, -ON(R2)CO-, -ON(R2)SO2-, -O-CON(R2)N(R3)CO-, -O-CON(R2)CO-, -O-CON(R2)SO2-, -CO-O-, -CO-CO-, -CO-CON(R2)N(R3)CO-, -CO-CON(R2)CO-, -CO-CON(R2)SO2-, -N(R2)O-, -N(R2)COCO-, -N(R2)N(R3)CO-, -N(R2)N(R3)SO2-, -N(R2)CON(R3)N(R4)CO-, -N(R2)CON(R3)CO-, -N(R2)CON(R3)SO2- or -N(R2)CON(R3)SO2N(R4)CO- in which R2, R3 and R4 are the same or different and each is hydrogen, alkyl, aralkyl, acyl or one of substituents α; B is a single bond, or a group of formula -N(R5)- or -N(R6)N(R5)- in which R5 and R6 are the same or different and each is hydrogen, alkyl, aralkyl, acyl or one of substituents α, or R5, together with R1 and the nitrogen atom to which they are bonded, may form a heterocyclic ring having from 5 to 7 ring atoms; or R1 may represent a group of formula -OR7, in which R7 is alkyl, alkenyl, aralkyl or one of substituents α; or R1 may represent a hydroxy group or a group of formula -OR7; and said substituents α are selected from aryl groups and heterocyclic groups] and pharmaceutically acceptable salts thereof have an excellent ability to enhance the activity of glutathione reductase and can therefore be used for the treatment and prevention of a variety of diseases including cataracts.

  式(I)化合物： 其中m 和 n 中的一个为 0，另一个为 0、1 或 2；k 为 0 或 1 至 12 的整数；R1 为氢、下文定义的取代基 α 之一或任选取代的烷基；A 是单键、氧原子、羰基或式-N(R2)CO-, -N(R2)CS-, -N(R2)SO2-, -CON(R2)N(R3)CO-, -CON(R2)CO-、-CON(R2)CS-，-CON(R2)SO2-，-O-CO-，-OON(R2)CO-，-OON(R2)SO2-，-O-CON(R2)N(R3)CO-，-O-CON(R2)CO-，-O-CON(R2)SO2-，-CO-O，-CO-CON(R2)N(R3)CO-、-CO-CON(R2)CO，-CO-CON(R2)SO2-，-N(R2)O-，-N(R2)CO-，-N(R2)N(R3)CO，-N(R2)N(R3)SO2-，-N(R2)CON(R3)N(R4)CO，-N(R2)CON(R3)CO、-N(R2)CON(R3)SO2-或-N(R2)CON(R3)SO2N(R4)CO-，其中 R2、R3 和 R4 可相同或不同，且各自为氢、烷基、芳基、酰基或取代基 α 之一；B 是单键，或者是式-N(R5)-或-N(R6)N(R5)-的基团，其中 R5 和 R6 相同或不同，且各自是氢、烷基、芳烷基、酰基或取代基 α 之一，或者 R5 与 R1 及其键合的氮原子可形成具有 5 至 7 个环原子的杂环；或者 R1 可代表式-OR7 的基团，其中 R7 是烷基、烯基、芳烷基或取代基 α 之一；或 R1 可代表羟基或式-OR7 的基团；且所述取代基 α 选自芳基和杂环基]及其药学上可接受的盐具有极佳的增强谷胱甘肽还原酶活性的能力，因此可用于治疗和预防包括白内障在内的多种疾病。
• Control of the electrostatic potential of nanoparticles
  申请人：Northwestern University

  公开号：US11150185B2

  公开（公告）日：2021-10-19

  The present technology is directed to the nanoparticles for use as molecular environmental sensors. The nanoparticles comprise a photoluminescence core and a plurality of ligands bound to the core and forming a quencher permeable ligand shell. The ligands comprise a reactive or charged moiety capable of being modulated between a first stand and a second state, and the proportion of ligands in each state determine the permeability of the ligand shell to a photoluminescence quencher.

  本技术涉及用作分子环境传感器的纳米颗粒。纳米颗粒包括一个光致发光核心和多个与核心结合并形成可渗透淬灭剂配体外壳的配体。配体包括可在第一状态和第二状态之间调节的活性或带电分子，而处于每种状态的配体比例决定了配体外壳对光致发光淬灭剂的渗透性。
• US6313164B1
  申请人：——

  公开号：US6313164B1

  公开（公告）日：2001-11-06
• Carbonic Anhydrase Activators: Gold Nanoparticles Coated with Derivatized Histamine, Histidine, and Carnosine Show Enhanced Activatory Effects on Several Mammalian Isoforms
  作者：Mohamed-Chiheb Saada、Jean-Louis Montero、Daniela Vullo、Andrea Scozzafava、Jean-Yves Winum、Claudiu T. Supuran

  DOI：10.1021/jm101284a

  日期：2011.3.10

  Lipoic acid moieties were attached to amine or amino acids showing activating properties against the zinc enzyme carbonic anhydrase (CA, EC 4.2.1.1). The obtained lipoic acid conjugates of histamine, L-histidine methyl ester, and L-carnosine methyl ester were attached to gold nanoparticles (NPs) by reaction with Au(III) salts in reducing conditions. The CA activators (CAAs) coated NPs showed low nanomolar activation (K(A)s of 1-9 nM) of relevant cytosolic, membrane-bound, mitochondrial, and transmembrane CA isoforms, such as CA I, II, IV, VA, VII, and XIV. These NPs also effectively activated CAs ex vivo., in whole blood experiments, with an increase of 200-280% of the CA activity. This is the first example of enzyme activation with nanoparticles and may lead to biomedical applications for condition in which the CA activity is diminished, such as aging, Alzheimer's disease, or CA deficiency syndrome.