(-)-aristeromycin acetonide | 174171-97-2

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: (-)-aristeromycin acetonide
• 英文别名: rel-((3AR,4R,6R,6aS)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)methanol；[(3aS,4R,6R,6aR)-4-(6-aminopurin-9-yl)-2,2-dimethyl-4,5,6,6a-tetrahydro-3aH-cyclopenta[d][1,3]dioxol-6-yl]methanol
• CAS: 174171-97-2
• 化学式: C₁₄H₁₉N₅O₃
• 分子量: 305.337
• InChiKey: ZPYBQTVZVONOSP-OYBPUVFXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  108
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (-)-aristeromycin acetonide 在 盐酸 作用下， 以 甲醇 为溶剂， 生成 芒霉素
  参考文献：
  名称：

  6'-β-氟阿霉素，6'-β-氟-5'-阿霉素和阿霉素的手性合成

  摘要：

  在C-6'位置取代的碳环核苷受到越来越多的关注。缺乏对生物学上有希望的6'-β-氟代阿霉素霉素的手性合成可及性。描述了其制备和5'-nor类似物的制备。一路走来，一种新的阿霉素霉素的方法作为必需的结构证明的产物出现了。

  DOI：

  10.1016/j.tetlet.2005.08.163
• 作为产物：
  描述：

  (3AR,4R,6R,6AS)-6-氨基-2,2-二甲基-六氢环戊二烯并[D][1,3]二氧杂环戊烯-4-基]甲醇 在 氨 、 对甲苯磺酸 作用下， 以 乙醇 为溶剂， 生成 (-)-aristeromycin acetonide
  参考文献：
  名称：

  Realisation of highly stereoselective dihydroxylation of a cyclopentene in the synthesis of (−)-aristeromycin

  摘要：

  2-呋喃基被用作阿里霉素4-位CH2OH的合成等价物，具有呋喃基的环戊烯的二羟基化高度立体选择性地进行，生成合成(α)-的关键二醇。阿里斯霉素。

  DOI：

  10.1039/a901819k

文献信息

• [EN] CYCLIC DINUCLEOTIDES AS STING AGONISTS<br/>[FR] DINUCLÉOTIDES CYCLIQUES UTILISÉS EN TANT QU'AGONISTES DE STING
  申请人：JANSSEN BIOTECH INC

  公开号：WO2019118839A1

  公开（公告）日：2019-06-20

  Disclosed are compounds, compositions and methods for treating of diseases, syndromes, or disorders that are affected by the modulation of STING. Such compounds are represented by Formula (I) as follows: wherein B2,X2, R2a, R2b, R2c, Z-M-Y, Y1-M1Z1, B1, X1, R1a, R1b, R1c are as defined herein.

  揭示了一种通过调节STING来治疗受影响的疾病、综合征或紊乱的化合物、组合物和方法。这些化合物由以下式（I）表示：其中B2、X2、R2a、R2b、R2c、Z-M-Y、Y1-M1Z1、B1、X1、R1a、R1b、R1c如本文所定义。
• Palladium-Catalyzed Enantioselective Synthesis of Carbanucleosides
  作者：Barry M. Trost、Robert Madsen、Simon D. Guile、Brian Brown

  DOI：10.1021/ja9938837

  日期：2000.6.1

  alkylation with phenylsulfonyl(nitro)methane 6. The nitrosulfone, thus obtained, served as a versatile intermediate for divergent synthesis in which the phenylsulfonyl(nitro)methyl group is a surrogate for the hydroxymethyl side chain. With the guanine-derived nucleobase 13, (−)-carbovir was obtained in only four steps from 10a. With 6-chloropurine as an adenine equivalent, the obtained nitrosulfone intermediate

  已开发出用于对映选择性合成多种碳核苷的一般策略。关键步骤是 Pd(0) 催化的 cis-3,5-dibenzoyloxycyclopent-2-ene 10a 与核碱基的对映选择性烯丙基胺化。使用鸟嘌呤衍生的核碱基 13 和手性配体 9，获得了 93-96% 的 ee，而 6-氯嘌呤和手性配体 8 获得了 94% 的 ee。该反应之后是与苯磺酰基（硝基）甲烷 6 进行第二次 Pd（0）催化的烯丙基烷基化反应。由此获得的硝基砜用作多用途中间体，用于发散合成，其中苯磺酰基（硝基）甲基是羟甲基侧链。使用鸟嘌呤衍生的核碱基 13，从 10a 仅通过四步即可获得 (-)-卡波韦。以 6-氯嘌呤作为腺嘌呤等价物，
• 5′-Amino-5′-deoxyaristeromycin and its antiviral properties
  作者：Vasanthakumar P Rajappan、Stewart W Schneller

  DOI：10.1016/j.bmc.2003.08.032

  日期：2003.11

  An efficient, three-step synthesis of 5'-amino-5'-deoxyaristeromycin (5), from a protected form of aristeromycin (6), is described. Compound 5 was evaluated against a large number of viruses. It showed weak activity towards vaccinia, herpes simplex virus 2, and cytomegalovirus. No other activity was observed. Compound 5 displayed some cytotoxicity towards the host cell lines human foreskin fibroblast

  描述了一种有效的，由受保护形式的阿霉素（6）合成5'-氨基-5'-脱氧阿霉素（5）的方法。针对大量病毒评估了化合物5。它对牛痘，单纯疱疹病毒2和巨细胞病毒的活性较弱。没有观察到其他活动。化合物5对人包皮成纤维细胞，Daudi和人T淋巴细胞（CEM）的宿主细胞系显示出一定的细胞毒性。
• Antitubercular Nucleosides That Inhibit Siderophore Biosynthesis:  SAR of the Glycosyl Domain
  作者：Ravindranadh V. Somu、Daniel J. Wilson、Eric M. Bennett、Helena I. Boshoff、Laura Celia、Brian J. Beck、Clifton E. Barry、Courtney C. Aldrich

  DOI：10.1021/jm061068d

  日期：2006.12.1

  Tuberculosis is the leading cause of infectious disease mortality in the world by a bacterial pathogen. We previously demonstrated that a bisubstrate inhibitor of the adenylation enzyme MbtA, which is responsible for the second step of mycobactin biosynthesis, exhibited potent antitubercular activity. Here we systematically investigate the structure-activity relationships of the bisubstrate inhibitor glycosyl domain resulting in the identification of a carbocyclic analogue that possesses a K-I(app) value of 2.3 nM and MIC99 values of 1.56 mu M against M. tuberculosis H37Rv. The SAR data suggest the intriguing possibility that the bisubstrate inhibitors utilize a transporter for entry across the mycobacterial cell envelope. Additionally, we report improved conditions for the expression of MbtA and biochemical analysis, demonstrating that MbtA follows a random sequential enzyme mechanism for the adenylation half-reaction.
• The sequel to a carbocyclic nucleoside synthesis: a divergent access to both arenediazonium ions and aryl triflates
  作者：C Picherit、F Wagner、D Uguen

  DOI：10.1016/j.tetlet.2004.01.147

  日期：2004.3

  Depending on the amount of acid used, treating aryl-dialkyl triazenes of general structure 3 with triflic acid resulted in the formation of either the corresponding arenediazonium triflates 4 or aryl triflates 8 apparently by two different pathways, the latter conversion being favoured at high acid concentration. (C) 2004 Elsevier Ltd. All rights reserved.