6-chloro-purine-2′-O-methyl-riboside | 51293-29-9

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 6-chloro-purine-2′-O-methyl-riboside
• 英文别名: (2R,3R,4R,5R)-5-(6-chloropurin-9-yl)-2-(hydroxymethyl)-4-methoxy-tetrahydrofuran-3-ol；1-(6-chloro-purin-9-yl)-O²-methyl-β-D-1-deoxy-ribofuranose；6-chloro-9-(2'-O-methyl-β-D-ribofuranosyl)-9H-purine；6-chloro-9-(2'-O-methyl-b-D-ribofuranosyl)-9H-purine；6-chloro-9-(2'O-methylbeta-D-ribofuranosyl)-9H-purine；(2R,3R,4R,5R)-5-(6-chloropurin-9-yl)-2-(hydroxymethyl)-4-methoxyoxolan-3-ol
• CAS: 51293-29-9
• 化学式: C₁₁H₁₃ClN₄O₄
• 分子量: 300.702
• InChiKey: QRTHLLMQALJIGF-IOSLPCCCSA-N

物化性质

• 沸点：
  572.0±60.0 °C(Predicted)
• 密度：
  1.82±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  103
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  6-chloro-purine-2′-O-methyl-riboside 生成 N-环己基-2'-O-甲基腺苷
  参考文献：
  名称：

  2'-O, N.sup.6 -disubstituted and 2'-O, N.sup.6, 2-trisubstituted

  摘要：

  腺苷衍生物的化学式为##STR1##其中R.sub.1是烯丙基，甲基烯丙基，直链或支链（C.sub.3-7）炔基，（C.sub.3-8）环烷基，或苯基单取代或独立地双取代，取代基为原子序数为9至35的卤素，（C.sub.1-4）烷基，（C.sub.1-4）烷氧基或CF.sub.3; R.sub.2是氢或C（.sub.1-4）烷基，R.sub.3是（C.sub.1-4）烷基，可用于保护血管内皮，降低血脂水平和治疗高血压。

  公开号：

  US05534503A1
• 作为产物：
  描述：

  6-氯嘌呤核苷 在 吡啶 、 四丁基氟化铵 、 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 生成 6-chloro-purine-2′-O-methyl-riboside
  参考文献：
  名称：

  5' 帽的化学酶修饰可维持翻译并增加 mRNA 的免疫原性

  摘要：

  真核 mRNA 是蛋白质替代疗法和疫苗接种的新兴方式。它们的 5' 帽对于 mRNA 翻译和免疫反应很重要，并且可以通过S-腺苷-l-甲硫氨酸 (AdoMet) 依赖性甲基转移酶 (MTase) 在不同位置自然甲基化。我们使用合成的 AdoMet 类似物报告了负责腺苷起始核苷酸N 6位甲基化的 MTase CAPAM 的共底物范围。化学酶炔丙基化能够产生位点特异性修饰的报告基因 mRNA。这些带帽炔丙基化的 mRNA 被有效翻译，并在人类细胞中显示出约 3 倍的免疫反应增强。当使用 SARS-CoV-2 的受体结合域 (RBD)（目前测试的用于 mRNA 疫苗接种的表位）时，观察到了相同的效果。因此，真核 mRNA 的位点特异性化学酶修饰可能是调节 mRNA 翻译和免疫反应以用于未来治疗应用的合适策略。

  DOI：

  10.1002/anie.202100352

文献信息

• 2'-O, N.sup.6 -disubstituted and 2'-O, N.sup.6, 2-trisubstituted
  申请人：Sandoz Ltd.

  公开号：US05534503A1

  公开（公告）日：1996-07-09

  Adenosines derivatives of the formula ##STR1## wherein R.sub.1 is allyl, methallyl, straight or branched chain (C.sub.3-7)alkynyl, (C.sub.3-8)cycloalkyl, or phenyl mono- or independently of one another di-substituted by halogen having an atomic number of from 9 to 35, (C.sub.1-4)alkyl, (C.sub.1-4)alkoxy, or CF.sub.3 ; R.sub.2 is hydrogen or C(.sub.1-4)alkyl, and R.sub.3 is (C.sub.1-4)alkyl, are useful for protecting vascular endothelium, for lowering blood lipid levels, and for treating raised blood pressure.

  腺苷衍生物的化学式为##STR1##其中R.sub.1是烯丙基，甲基烯丙基，直链或支链（C.sub.3-7）炔基，（C.sub.3-8）环烷基，或苯基单取代或独立地双取代，取代基为原子序数为9至35的卤素，（C.sub.1-4）烷基，（C.sub.1-4）烷氧基或CF.sub.3; R.sub.2是氢或C（.sub.1-4）烷基，R.sub.3是（C.sub.1-4）烷基，可用于保护血管内皮，降低血脂水平和治疗高血压。
• Adenosine derivatives and pharmaceutical composition thereof
  申请人：Nippon Zoki Pharmaceutical Co., Ltd.

  公开号：US04985409A1

  公开（公告）日：1991-01-15

  The present invention relates to novel adenosine derivatives having the formula (I): ##STR1## wherein R is a lower alkyl group; R' is hydrogen or a lower alkyl group; X is a cycloalkyl group, an alkyl group having at least one hydroxy group, an alkyl group having at least one phenyl group, a bicycloalkyl group, a naphthylalkyl group, an acenaphthylenylalkyl group or a group of the formula (II) or (III); ##STR2## Z is hydrogen, a hydroxy group or a lower alkoxy group, Q is hydrogen or a hydroxy group, A is --CH.sub.2 --, --O--, --S-- or shows a direct connection; Y is --(CH.sub.2).sub.n -- or shows a direct connection; n is an integer of 1 to 3; and the broken line is a double bond or a single bond. and pharmaceutically acceptable salt thereof, which are useful as antihypertensive agents.

  本发明涉及具有以下式子（I）的新型腺苷衍生物： ##STR1## 其中R是较低的烷基；R'是氢或较低的烷基；X是环烷基，具有至少一个羟基的烷基，具有至少一个苯基的烷基，双环烷基，萘基烷基，芴基烷基或式子（II）或（III）的基团； ##STR2## Z是氢，羟基或较低的烷氧基，Q是氢或羟基，A是--CH.sub.2 --，--O--，--S--或显示直接连接；Y是--(CH.sub.2).sub.n --或显示直接连接；n是1到3的整数；断线是双键或单键。以及其药学上可接受的盐，它们可用作降压剂。
• DI (1R)-(-)camphosulfonic acid) salt, preparation thereof and use thereof
  申请人：Rhone-Poulenc Rorer Pharmaceuticals Inc.

  公开号：US05652366A1

  公开（公告）日：1997-07-29

  This invention relates to di[(1 R)-(-)-camphosulfonic acid) salt of [1S-[1.alpha.,2.beta.,3.beta.,4.alpha.,(S*)]]-4-[7-[[2-(3-chloro-2-thienyl )-1-ethylethyl]amino]3 H-imidazo[4,5-b]pyridin-3-yl]-N-ethyl-2,3-dihydroxycyclopentanecarboxamide , and a process for preparing the compound, comprising reacting a reaction mixture of (-)-1.beta.-N-ethyl-2.alpha.,3.alpha.-isopropylidenedioxy-4.beta.-[3-amino -4-[2-(5-chloro-2-thienyl)-(1R)-1-ethylethyl]amino-2-pyridyl]aminocyclopent anecarboxamide and formamidine acetate, and then treating the reaction mixture with (1 R)-(-)-10-camphorsulfonic acid. The salt is useful in purifying [1 S-[1.alpha.,2.beta.,3.beta.,4.alpha.,(S*)]]-4-[7-[[2-(3-chloro-2-thienyl)- 1-ethylethyl]amino]-3 H-imidazo[4,5-b]pyridin-3-yl]-N-ethyl-2,3-dihydroxycyclopentanecarboxamide which possesses adenosine agonist activity and is useful as an anti-hypertensive, cardioprotective, anti-ischemic, and antilipolytic agent.

  本发明涉及[(1R)-(-)-蒎磺酸]盐酸盐的[1S-[1α，2β，3β，4α，(S*)]]-4-[7-[[2-(3-氯-2-噻吩基)-1-乙基乙基]氨基]3H-咪唑[4,5-b]吡啶-3-基]-N-乙基-2,3-二羟基环戊烷羧酰胺，以及一种制备该化合物的方法，包括将(-)-1β-N-乙基-2α，3α-异丙基亚甲基-4β-[3-氨基-4-[2-(5-氯-2-噻吩基)-(1R)-1-乙基乙基]氨基-2-吡啶基]氨基环戊烷羧酰胺和甲酸甲酯的反应混合物反应，然后用(1R)-(-)-蒎磺酸处理反应混合物。该盐酸盐在纯化[1S-[1α，2β，3β，4α，(S*)]]-4-[7-[[2-(3-氯-2-噻吩基)-1-乙基乙基]氨基]-3H-咪唑[4,5-b]吡啶-3-基]-N-乙基-2,3-二羟基环戊烷羧酰胺中很有用，该化合物具有腺苷受体激动剂活性，并且可用作抗高血压、心脏保护、抗缺血和抗脂解剂。
• Compounds having antihypertensive, cardioprotective anti-ischemic and antilipolytic properties
  申请人：——

  公开号：US20020099030A1

  公开（公告）日：2002-07-25

  This invention relates to adenosine derivatives and analogues which possess biological activity and are useful as anti-hypertensive, cardioprotective, anti-ischemic, and antilipolytic agents, to pharmaceutical compositions including such compounds, and to their use in treating hypertension, myocardial ischemia, ameliorating ischemic injury and myocardial infarct size consequent to myocardial ischemia, and treating hyperlipidemia and hypercholesterolemia, and to methods and intermediates used in the preparation of such compounds.

  本发明涉及腺苷衍生物和类似物，具有生物活性，可用作抗高血压、心脏保护、抗缺血和抗脂解作用的药物，包括这些化合物的制药组合物，以及它们在治疗高血压、心肌缺血、改善缺血损伤和心肌梗死大小，治疗高脂血症和高胆固醇血症方面的用途，以及用于制备这些化合物的方法和中间体。
• Compounds having antihypertensive, cardioprotective, anti-ischemic and
  申请人：Rhone-Poulenc Rorer Pharmaceuticals Inc.

  公开号：US05561134A1

  公开（公告）日：1996-10-01

  Compounds of the Formula ##STR1## wherein: K is N or N.fwdarw.O; Q is CH.sub.2 or O; T is ##STR2## or R.sub.3 O--CH.sub.2 ; X is a straight or branched chain alkylene, cycloalkylene or cycloalkenylene group, each of which is optionally substituted by at least one CH.sub.3, CH.sub.3 CH.sub.2, Cl, F, CF.sub.3 or CH.sub.3 O; Y is NR.sub.4, O or S; a=0 or 1; Z is of the formula ##STR3## Z.sub.1 is N, CR.sub.5, (CH).sub.m --CR.sub.5 or (CH).sub.m --N, m being 1 or 2; Z.sub.2 is N, NR.sub.6, O or S, n being 0 or 1; R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5 and R.sub.6 are independently H, alkyl, aryl or heterocyclyl; R.sub.a and R.sub.b are independently H, OH, alkyl, hydroxyalkyl, alkyl mercaptyl, thioalkyl, alkoxy, alkyoxyalkyl, amino, alkyl amino, carboxyl, acyl, halogen, carbamoyl, alkyl carbamoyl, aryl or heterocyclyl; and R' and R" are independently hydrogen, alkyl, aralkyl, carbamoyl, alkyl carbamoyl, dialkylcarbamoyl, acyl, alkoxycarbonyl aralkoxycarbonyl, aryloxycarbonyl, or R' and R" together may form ##STR4## where R.sub.c is hydrogen or alkyl, ##STR5## where R.sub.d and R.sub.e are independently hydrogen, alkyl, or together with the carbon atom to which they are attached may form a 1,1-cycloalkyl group; provided that when X is straight chain alkylene and Q is oxygen, then Z represents a heterocyclyl including at least two heteroatoms, which are adenosine agonists useful as antihypertensive, cardioprotective, antiischemic, and antilipolytic agents, pharmaceutical compositions including such compounds, and their use in treating hypertension, myocardial ischemia, ameliorating ischemic injury and myocardial infarct size consequent to myocardial ischemia, hyperlipidemia and hypercholesterolemia are claimed.

  本发明涉及式##STR1##的化合物，其中：K为N或N.fwdarw.O；Q为CH.sub.2或O；T为##STR2##或R.sub.3 O--CH.sub.2；X为直链或支链烷基，环烷基或环烯烃基，每个基都可以被至少一个CH.sub.3、CH.sub.3 CH.sub.2、Cl、F、CF.sub.3或CH.sub.3 O取代；Y为NR.sub.4、O或S；a=0或1；Z为式##STR3##Z.sub.1为N、CR.sub.5、(CH).sub.m --CR.sub.5或(CH).sub.m --N，其中m为1或2；Z.sub.2为N、NR.sub.6、O或S，其中n为0或1；R.sub.1、R.sub.2、R.sub.3、R.sub.4、R.sub.5和R.sub.6独立地为H、烷基、芳基或杂环基；R.sub.a和R.sub.b独立地为H、OH、烷基、羟基烷基、烷基巯基、硫代烷基、烷氧基、烷氧基烷基、氨基、烷基氨基、羧基、酰基、卤素、氨基甲酰基、芳基或杂环基；R'和R"独立地为氢、烷基、芳基烷基、氨甲酰基、烷基氨甲酰基、二烷基氨甲酰基、酰基、烷氧羰基、芳基氧羰基，或者R'和R"一起形成##STR4##其中R.sub.c为氢或烷基，##STR5##其中R.sub.d和R.sub.e独立地为氢、烷基，或者与它们所连接的碳原子一起形成1,1-环烷基；但当X为直链烷基且Q为氧时，Z表示至少包含两个杂原子的杂环基，这些化合物是腺苷受体激动剂，可用作抗高血压、心脏保护、抗缺血和抗脂解剂，还包括这些化合物的制药组合物以及它们在治疗高血压、心肌缺血、改善缺血性损伤和心肌梗塞大小以及高脂血症和高胆固醇血症方面的用途。