8-碘腺苷 | 31281-88-6

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 中文名称: 8-碘腺苷
• 英文名称: 8-iodoadenosine
• 英文别名: 8-Iodadenosin；(2R,3R,4S,5R)-2-(6-amino-8-iodo-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol；(2R,3R,4S,5R)-2-(6-amino-8-iodopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
• CAS: 31281-88-6
• 化学式: C₁₀H₁₂IN₅O₄
• 分子量: 393.141
• InChiKey: CYOIMLAHGVOKIG-UUOKFMHZSA-N

物化性质

• 沸点：
  730.4±70.0 °C(Predicted)
• 密度：
  2.69±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  140
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  三甲基氯硅烷 、 8-碘腺苷 在 吡啶 、 六甲基二硅氮烷 作用下， 反应 6.0h， 以96%的产率得到8-iodo-2',3',5'-(triOTMS)adenosine
  参考文献：
  名称：

  Synthèe, caractérisation et propriétés cytotoxiques des premiers ‘métallocénonucléosides’

  摘要：

  The synthesis of the first 'metallocenonucleosides' (nucleosides containing a metallocenic moiety in their framework) of the formula Ns-C = C-Fc, Ns-CH = CH-Fc and Ns-CH2-CH2-Fc (Ns = uridine, deoxyuridine, adenosine; Fc: C5H4FeC5H5) has been conducted in the presence of palladium salt according to the following routes: i) reaction of a 5-chloromercuri-nucleoside on ethynylferrocene; ii) hydrozirconation (Schwartz' reagent) of ethynylferrocene followed by the reaction of a 5-halogeno nucleoside; iii) direct coupling between ethynylferrocene and a 5-halogeno nucleoside. The same procedures allowed the synthesis of the corresponding 'metallocenonucleobases' Nb-C = C-Fc, Nb-CH = CH-Fc and NbCH2CH2Fc (Nb = uracil, cytosine, adenine) which have also been prepared by acid solvolysis of the nucleosides precursors. The compounds obtained were purified by HPLC technique and were characterized by H-1 NMR and mass spectrometry. The cytotoxicity in vitro has been studied on L 1210 cells. Only modest activity has been observed.

  DOI：

  10.1016/0223-5234(91)90070-4

文献信息

• ANTI-MICROBIAL AGENTS AND USES THEREOF
  申请人：Tan Derek Shieh

  公开号：US20090170805A1

  公开（公告）日：2009-07-02

  Many pathogens, including Mycobacterium tuberculosis and Yersinia pestis , rely on an iron acquisition system based on siderophores, secreted iron-chelating compounds with extremely high Fe(III) affinity. The compounds of the invention are inhibitors of domain salicylation enzymes, which catalyze the salicylation of an aroyl carrier protein (ArCP) domain to form a salicyl-ArCP domain thioester intermediate via a two-step reaction. The compounds include the intermediate mimic 5′-O—[N-(salicyl)sulfamoyl]-adenosine (salicyl-AMS) and analogs thereof. These compounds are inhibitors of the salicylate activity of MbtA, YbtE, PchD, and other domain salicylation enzymes involved in the biosynthesis of siderophores. Therefore, these compounds may be used in the treatment of infection caused by microorganisms which rely on siderphore-based iron acquisition systems. Pharmaceutical composition and methods of using these compounds to treat or prevent infection are also provided as well as methods of preparing the inventive compounds.
• US8461128B2
  申请人：——

  公开号：US8461128B2

  公开（公告）日：2013-06-11
• US8946188B2
  申请人：——

  公开号：US8946188B2

  公开（公告）日：2015-02-03
• [EN] ANTI-MICROBIAL AGENTS AND USES THEREOF<br/>[FR] AGENTS ANTIMICROBIENS ET UTILISATIONS DE CEUX-CI
  申请人：SLOAN KETTERING INST CANCER

  公开号：WO2006113615A2

  公开（公告）日：2006-10-26

  [EN] Many pathogens, including Mycobacterium tuberculosis and Yersinia pestis, rely on an iron acquisition system based on siderophores, secreted iron-chelating compounds with extremely high Fe(III) affinity. The compounds of the invention are inhibitors of domain salicylation enzymes, which catalyze the salicylation of an aroyl carrier protein (ArCP) domain to form a salicyl-ArCP domain thioester intermediate via a two-step reaction. The compounds include the intermediate mimic 5 '-O- [N- (salicyl)sulfamoyl] -adenosine (salicyl-AMS) and analogs thereof. These compounds are inhibitors of the salicylate activity of MbtA, YbtE, PchD, and other domain salicylation enzymes involved in the biosynthesis of siderophores. Therefore, these compounds may be used in the treatment of infection caused by microorganisms which rely on siderphore-based iron acquisition systems. Pharmaceutical composition and methods of using these compounds to treat or prevent infection are also provided as well as methods of preparing the inventive compounds.
  [FR] Nombre de pathogènes, notamment Mycobacterium tuberculosis et Yersinia pestis, s'appuient sur un système d'acquisition du fer par l'intermédiaire de sidérophores, sécrétés par des composés chélateurs du fer, avec une affinité extrêmement élevée pour Fe(III). Les composés décrits dans la présente invention sont des inhibiteurs des enzymes de salicylation de domaines qui catalysent la salicylation d'un domaine protéique ArCP (aroyl carrier protein: protéine transporteuse d'aroyle) pour former un intermédiaire thioester d'un domaine salicyl-ArCP au moyen d'une réaction à deux étapes. Ces composés comprennent le mimétique intermédiaire 5 '-O- [N- (salicyl)sulfamoyl] -adénosine (salicyl-AMS) et des analogues de celui-ci. Ces composés sont des inhibiteurs de l'activité salicylate de MbtA, YbtE, PchD, et d'autres enzymes de salicylation de domaines impliqués dans la biosynthèse des sidérophores. Ces composés peuvent par conséquent être utilisés pour le traitement des infections causées par des micro-organismes qui dépendent de systèmes d'acquisition de fer par l'intermédiaire de sidérophores. L'invention concerne également une composition pharmaceutique et des méthodes d'utilisation de ces composés pour le traitement ou la prévention des infections, ainsi que des procédés de préparation des composés décrits.
• [EN] BIOMEDICAL DEVICE IMPLANTABLE IN BONE AND/OR CARTILAGINOUS TISSUE, AND CORRESPONDING METHOD TO MANUFACTURE SAID BIOMEDICAL DEVICE<br/>[FR] DISPOSITIF BIOMÉDICAL IMPLANTABLE DANS L'OS ET/OU LE TISSU CARTILAGINEUX, ET PROCÉDÉ CORRESPONDANT POUR FABRIQUER LEDIT DISPOSITIF BIOMÉDICAL
  申请人：GALLI CARLO

  公开号：WO2014128289A1

  公开（公告）日：2014-08-28

  Aptamers for use in coating biomaterials, in particular for example for making biomedical devices which can be implanted in tissue, or tissue implants, corresponding method for coating biomaterials using aptamers and method for making biomedical devices which can be implanted in tissue, or tissue implants.