脱氧菇嘌甲酯 | 33231-14-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 中文名称: 脱氧菇嘌甲酯
• 英文名称: 4-(6-aminopurin-9-yl)-2-hydroxybutyric acid methyl ester
• 英文别名: methyl 4-(adenin-9-yl)-2-hydroxybutanoate；(rac)-DZ2002；DZ2002；4-(6-amino-purin-9-yl)-2-hydroxy-butyric acid methyl ester；9H-Purine-9-butanoic acid, 6-amino-alpha-hydroxy-, methyl ester；methyl 4-(6-aminopurin-9-yl)-2-hydroxybutanoate
• CAS: 33231-14-0
• 化学式: C₁₀H₁₃N₅O₃
• 分子量: 251.245
• InChiKey: HNKGMGPCSSJYOT-UHFFFAOYSA-N

物化性质

• 沸点：
  529.3±60.0 °C(Predicted)
• 密度：
  1.58±0.1 g/cm3(Predicted)
• 溶解度：
  二甲基亚砜：≥ 61 mg/ml（242.80 mM）

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  116
• 氢给体数：
  2
• 氢受体数：
  7

安全信息

• 储存条件：
  2-8℃

制备方法与用途

DZ2002是一种高效可逆性抑制剂，能够特异性作用于腺苷同型半胱氨酸水解酶（SAHH；AdoHcy Hydrolase），其Ki值为17.9纳摩尔。

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  ——	4-(6-amino-purin-9-yl)-2-hydroxy-butyric acid	33231-13-9	C9H11N5O3	237.218
  ——	4-(6-aminopurin-9-yl)-2-oxobutyric acid methyl ester	1092082-09-1	C10H11N5O3	249.229
  ——	9-[3-O-(1-ethoxyethyl)-3,4-dihydroxybutyl]adenine	862460-34-2	C13H21N5O3	295.341

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	4-(6-amino-purin-9-yl)-2-hydroxy-butyric acid	33231-13-9	C9H11N5O3	237.218

反应信息

• 作为反应物：
  描述：

  脱氧菇嘌甲酯 在 sodium hydroxide 、 水 、 盐酸 、 氨 作用下， 以 甲醇 、 水 为溶剂， 反应 6.0h， 以75%的产率得到4-(adenin-9-yl)-2-hydroxybutanoic acid ammonium salt
  参考文献：
  名称：

  Reversible inhibitors of SAH hydrolase and uses thereof

  摘要：

  本发明提供了用于可逆地抑制S-腺苷基-L-同型半胱氨酸（SAH）水解酶的组合物和方法。本发明的化合物可与抗出血性病毒感染药物、免疫抑制剂、降低同型半胱氨酸的药物或抗肿瘤剂结合使用。本发明的组合物和方法可用于预防和治疗出血性病毒感染、自身免疫疾病、自体移植排斥、肿瘤、高同型半胱氨酸尿症、心血管疾病、中风、阿尔茨海默病或糖尿病。

  公开号：

  US20040204429A1
• 作为产物：
  描述：

  4-(6-aminopurin-9-yl)-2-oxobutyric acid methyl ester 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以60%的产率得到脱氧菇嘌甲酯
  参考文献：
  名称：

  Synthesis and biological evaluation of immunosuppressive agent DZ2002 and its stereoisomers

  摘要：

  DZ2002 and its related stereoisomers were efficiently synthesized. The optical data of (R)- and (S)-DZ2002 were disclosed here for the first time. Their inhibitory potency was evaluated on SAHase and MLR assay in the mean time. In accordance with respective inhibitory potency of SAHase, the immunosuppressive potency order was demonstrated as (S)-Z2002 > (Rac)-DZ2002 > (R)-DZ2002 > (Keto)DZ2002. These results indicate (S)-configuration of 2-chiral center in DZ2002 is important for binding with SAHase. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.09.017

文献信息

• THERAPEUTIC AGENT FOR CEREBRAL INFARCTION
  申请人：Nakao Akira

  公开号：US20120196824A1

  公开（公告）日：2012-08-02

  The invention provides a therapeutic drug for ischemic stroke. The therapeutic drug has the formula (I) wherein each symbol is as defined herein, or a pharmacologically acceptable salt thereof, or a solvate thereof, as an active ingredient.

  这项发明提供了一种用于缺血性中风的治疗药物。该治疗药物具有如下式（I）的化学式，其中每个符号如本文所定义，或其药理学上可接受的盐，或其溶剂化物，作为活性成分。
• Reversible inhibitors of S-adenosyl-L-homocysteine hydrolase and uses thereof
  申请人：Yuan Chong-Sheng

  公开号：US20050182075A1

  公开（公告）日：2005-08-18

  The present invention provides compositions and methods for reversibly inhibiting S-adenosyl-L-homocysteine (SAH) hydrolase. The compounds of the present invention can be used in combination with an anti-hemorrhagic viral infection agent, an immunosuppressant, a homocysteine lowering agent, or an anti-neoplasm agent. The compositions and methods of the present invention can be used for the prevention and treatment of hemorrhagic virus infection, autoimmune diseases, autograft rejection, neoplasm, hyperhomocysteineuria, cardiovascular disease, stroke, Alzheimer's disease, or diabetes.

  本发明提供了可逆抑制S-腺苷基-L-同型半胱氨酸（SAH）水解酶的组合物和方法。本发明的化合物可以与抗出血性病毒感染药物、免疫抑制剂、降低同型半胱氨酸的药物或抗肿瘤药物结合使用。本发明的组合物和方法可用于预防和治疗出血性病毒感染、自身免疫性疾病、自体移植排斥、肿瘤、高同型半胱氨酸血症、心血管疾病、中风、阿尔茨海默病或糖尿病。
• A METHOD FOR PREPARING 4-Ý9-(6-AMINOPURINE)¨-2-(S)-HYDROXYL-BUTYRIC ACID METHYL ESTER
  申请人：SHANGHAI INSTITUTE OF MATERIA MEDICA, CHINESE ACADEMY OF SCIENCES

  公开号：EP2230239A1

  公开（公告）日：2010-09-22

  The present invention discloses a novel method for preparing and purifying 4-(6-Amino-purin-9-yl)-2(S)-hydroxy-butyric acid methyl ester. The preparation started from cheap and easily available L-malic acid, which was transformed to intermediate I after simultaneous protection of the groups of 1-carboxyl and 2-hydroxyl. The intermediate I was selectively reduced to intermediate alcohol II, whose hydroxyl group was further transformed to an easily leaving group to afford intermediate III. The intermediate III was nucleophilically substituted with adenine to afford intermediate IV The intermediate IV was deprotected and methyl-esterified simultaneously in methanol in the presence of an acid or a base to afford crude 4-(6-Amino-purin-9-yl)-2(S)-hydroxy-butyric acid methyl ester, which was purified by recrystallization to afford the purified product. Comparing with the prior preparation methods, the present method has advantages in low cost, mild conditions, high retention of the chiral center during the reaction, high productivity, great improvement in the quality and yield of the product and great decrease in cost, and thus is suitable for the production on a large scale.

  本发明公开了一种制备和纯化 4-(6-氨基-嘌呤-9-基)-2(S)-羟基丁酸甲酯的新方法。该制备方法从廉价易得的 L-苹果酸开始，在同时保护 1-羧基和 2-羟基后将其转化为中间体 I。中间体 I 被选择性地还原成中间体醇 II，其羟基进一步转化为易离去基团，得到中间体 III。中间体 IV 在甲醇中，在酸或碱的存在下同时进行脱保护和甲基酯化，得到粗制的 4-(6-氨基-嘌呤-9-基)-2(S)-羟基丁酸甲酯。与之前的制备方法相比，本方法具有成本低、条件温和、反应过程中手性中心保留率高、生产率高、产品质量和收率大大提高、成本大大降低等优点，适合大规模生产。
• Application of methyl 4-[9-(6-aminopuryl)]-2(s)-hydroxybutyrate in preparation of medicament for treating psoriasis and vitiligo
  申请人：SHANGHAI INSTITUTE OF MATERIA MEDICA, CHINESE ACADEMY OF SCIENCES

  公开号：US11045475B2

  公开（公告）日：2021-06-29

  Provided in the present invention is a use of methyl 4-[9-(6-aminopuryl)]-2(s)-hydroxybutyrate in the preparation of a medicament for treating psoriasis and vitiligo. More specifically, the present invention uses mice whose psoriasis is induced by an imiquimod cream to observe a changing condition in skin lesions on the psoriasis-like mice, according to a psoriasis skin lesion area of the mice and grading standards for disease severity; the present invention also observes a proportion of lymphocytes in the spleens and cytokines in skin lesion tissues of the mice. A good therapeutic effect may be obtained by treating typical cases of vitiligo with an ointment of methyl 4-[9-(6-aminopuryl)]-2(s)-hydroxybutyrate. Results show that methyl 4-[9-(6-aminopuryl)]-2(s)-hydroxybutyrate used in the present invention has a good therapeutic effect on psoriasis and vitiligo, as well as a favorable prospect in clinical application.

  本发明提供了 4-[9-(6-氨基戊酰)]-2(s)-羟基丁酸甲酯在制备治疗银屑病和白癜风的药物中的用途。更具体地说，本发明利用咪喹莫特乳膏诱发银屑病的小鼠，根据小鼠的银屑病皮损面积和疾病严重程度的分级标准，观察银屑病样小鼠皮损的变化情况；本发明还观察小鼠脾脏中淋巴细胞的比例和皮损组织中细胞因子的比例。用 4-[9-(6-氨基戊酰)]-2(s)-羟基丁酸甲酯软膏治疗典型的白癜风病例，可获得良好的治疗效果。结果表明，本发明中使用的 4-[9-(6-氨基戊酰)]-2(s)-羟基丁酸甲酯对牛皮癣和白癜风有良好的治疗效果，临床应用前景广阔。
• [EN] USE OF 4-[9-(6-AMINOPURINYL)]-2(S)-HYDROXYMETHYL BUTYRATE FOR PREPARING OPHTHALMIC PREPARATIONS<br/>[FR] UTILISATION DE 4-[9-(6-AMINOPURINYL)]-2 (S)-HYDROXYMÉTHYL BUTYRATE POUR LA PRÉPARATION DE PRÉPARATIONS OPHTALMIQUES<br/>[ZH] 4-[9-(6-氨基嘌呤基)]-2(S)-羟基丁酸甲酯用于制备眼科制剂的用途
  申请人：SHANGHAI INST MATERIA MEDICA CAS

  公开号：WO2021047464A1

  公开（公告）日：2021-03-18

  涉及4-[9-(6-氨基嘌呤基)]-2(S)-羟基丁酸甲酯用于制备眼科制剂的用途，更具体地，涉及4-[9-(6-氨基嘌呤基)]-2(S)-羟基丁酸甲酯在制备预防或治疗由泪液分泌不足所致眼部炎症损伤的眼科制剂中的用途。