(1R,3S)-(-)-3-hydroxycyclopentyl acetate | 149342-57-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,3S)-(-)-3-hydroxycyclopentyl acetate
• 英文别名: (1R,3S)-1-acetoxy-3-hydroxycyclopentane；(1R,3S)-(-)-1-acetoxycyclopentan-3-ol；cis-3-Hydroxy-cyclopentylacetat；(1S,3R)-cis-3-acetoxycyclopentan-1-ol；(-)-cis-3-acetoxy-cyclopentanol；[(1R,3S)-3-hydroxycyclopentyl] acetate
• CAS: 149342-57-4
• 化学式: C₇H₁₂O₃
• 分子量: 144.17
• InChiKey: BWFGXNSNXSWGQA-NKWVEPMBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1R,3S)-(-)-3-hydroxycyclopentyl acetate 在 sodium hydride 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 52.0h， 生成 9N-[(1'R,3'R)-trans-3'-acetoxycyclopentanyl]adenine
  参考文献：
  名称：

  碳环核苷作为人类肿瘤坏死因子-α产生的抑制剂：（3-羟基环戊基）腺嘌呤的立体异构体的影响。

  摘要：

  合成了一系列四个结构相关的碳环核苷（6a，6b，10a和10b），并评估了它们抑制肿瘤坏死因子-α（TNF-α），白介素-1β（IL-1 beta）和从人类原代巨噬细胞中产生白介素6（IL-6）。这些化合物对IL-1β和IL-6的产生几乎没有影响。已确定化合物10a是最有效的TNF-α抑制剂（IC50 = 10 microM），与其对映异构体10b或其非对映异构体6a和6b相比，活性高2至5倍。此外，还测试了这些化合物保护小鼠免受脂多糖（LPS）和D-半乳糖胺（D-Gal）致命攻击的能力。

  DOI：

  10.1021/jm950906t
• 作为产物：
  描述：

  3,5-dibromocyclopentene 在 Pancreatin 、 sodium tetrahydroborate 、 苄基三乙基氯化铵 、 氢气 、 nickel(II) acetate tetrahydrate 、 potassium hydrogencarbonate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 叔丁醇 为溶剂， 20.0 ℃ 、689.49 kPa 条件下， 反应 4.0h， 生成 (1R,3S)-(-)-3-hydroxycyclopentyl acetate
  参考文献：
  名称：

  Development of the Carbocyclic Nucleoside MDL 201449A:  A Tumor Necrosis Factor-α Inhibitor

  摘要：

  An efficient synthesis of (1S,4R)-(-)-4-tert-butyldimethylsilyloxy-2-cyclopentenyl acetate and (1R,4S)-(-)-4-tert-butyldimethylsilyloxy-2-cyclopentenol is described utilizing a furfuryl alcohol rearrangement, followed by a lithium aluminum hydride reduction with high facial selectivity and an efficient enzymatic resolution with pancreatin. Both of these intermediates were successfully utilized in the preparation of the carbocyclic nucleoside 9N-[(1'R,3'R)-trans-3'-hydroxycyclopentanyl]adenine hydrochloride, an agent which inhibits the formation of tumor necrosis factor-alpha.

  DOI：

  10.1021/op9701245

文献信息

• Preparation of cis-4-O-protected-2-cyclopentenol derivatives
  申请人：Hoechst Marion Roussel Inc.

  公开号：US05728899A1

  公开（公告）日：1998-03-17

  The present invention relates to a novel process for preparing cis-4-O-protected-substituted-2-cyclopentenol derivatives comprising, a) dissolving a 4-O-protected-2-cyclopentenone in a suitable organic solvent; and b) treating the solution with a suitable Lewis acid and a suitable reducing agent at a temperature of from about -100.degree. C. to about 20.degree. C. The cis-4-O-protected-substituted-2-cyclopentenol derivatives are useful intermediates in the preparation of various cyclopentanyl and cyclopentenyl purine analogs which are useful as immunosuppressants and in the preparation of various prostaglandins.

  本发明涉及一种制备顺式-4-O-保护取代-2-环戊烯醇衍生物的新方法，包括以下步骤：a) 将4-O-保护的2-环戊烯酮溶解于适宜的有机溶剂中；b) 在约-100°C至约20°C的温度下，向该溶液中加入适宜的路易斯酸和适宜的还原剂。顺式-4-O-保护取代-2-环戊烯醇衍生物是制备各种环戊基和环戊烯基嘌呤类似物的有用中间体，这些类似物可作为免疫抑制剂，并用于制备各种前列腺素。
• Trans cyclopentanyl purine analogs useful as immunosuppressants
  申请人：Hoechst Marion Roussel, Inc.

  公开号：US05723466A1

  公开（公告）日：1998-03-03

  This invention relates to Trans cyclopentanyl purine analogs of the formula (1) ##STR1## wherein the substituent in the 3-position on the cyclopentanyl ring is in the Trans configuration relative to the bicyclic substituent, Y.sub.3, Y.sub.5 and Y.sub.9 are each nitrogen and Y.sub.7 and Y.sub.8 are a CH group, R is a C.sub.1 -C.sub.7 alkyl acyl or aryl acyl, Q is NH.sub.2, halogen or hydrogen, Z is hydrogen, halogen, or NH.sub.2 ; or a pharmaceutically-acceptable salt thereof, and to their use as immunosuppressants.

  本发明涉及公式（1）的Trans环戊酰基嘌呤类似物 ##STR1## 其中，环戊酰基上的3位取代基与双环取代基Y.sub.3，Y.sub.5和Y.sub.9相对处于Trans构型，Y.sub.7和Y.sub.8为CH基，R为C.sub.1-C.sub.7烷酰基或芳基酰基，Q为NH.sub.2，卤素或氢，Z为氢，卤素或NH.sub.2；或其药学上可接受的盐，并用作免疫抑制剂。
• Purine derivatives as a2a agonists
  申请人：Fairhurst Robin Alec

  公开号：US20100240680A1

  公开（公告）日：2010-09-23

  Compounds of formula (I): or stereoisomers or pharmaceutically acceptable salts thereof, wherein W, R 1 , R 2 and R 3 have the meanings as indicated in the specification, are useful for treating conditions mediated by activation of the adenosine A 2A receptor, especially inflammatory or obstructive airways diseases. Pharmaceutical compositions that contain the compounds and a process for preparing the compounds are also described.

  式(I)的化合物或其立体异构体或药学上可接受的盐，其中W，R1，R2和R3的含义如说明书中所示，可用于治疗通过激活腺苷A2A受体介导的疾病，特别是炎症或阻塞性气道疾病。还描述了含有该化合物的药物组合物和制备该化合物的过程。
• Novel trans cyclopentanyl purine analogs useful as immunosuppressants
  申请人：HOECHST MARION ROUSSEL, INC.

  公开号：EP0545413A1

  公开（公告）日：1993-06-09

  This invention relates to novel trans cyclopentanyl purine analogs of the formula (1) wherein    the substituent in the 3-position on the cyclopentanyl ring is in the Trans configuration relative to the bicyclic substituent,    Y₃, Y₅ Y₇, Y₈ and Y₉ are each independently nitrogen or a CH group,    R is a hydrogen, a C₁-C₇ alkyl acyl or aryl acyl,    Q is NH₂, halogen or hydrogen,    Z is hydrogen, halogen, or NH₂; or a pharmaceutically-acceptable salt thereof, and to their use as immunosuppressants.

  本发明涉及式 (1) 的新型反式环戊基嘌呤类似物 其中 环戊烷环上 3 位的取代基相对于双环取代基为反式构型、 Y₃、Y₅、Y₇、Y₈ 和 Y𠢙 各自独立地为氮或 CH 基团、 R 是氢、C₁-C₇ 烷酰基或芳酰基、 Q 是 NH₂、卤素或氢、 Z 是氢、卤素或 NH₂； 或其药学上可接受的盐，以及它们作为免疫抑制剂的用途。
• Purine derivatives as A2a agonists
  申请人：Novartis AG

  公开号：EP1889846A1

  公开（公告）日：2008-02-20

  Compounds of formula (I) or stereoisomers or pharmaceutically acceptable salts thereof, wherein W, R1, R2 and R3 have the meanings as indicated in the specification, are useful for treating conditions mediated by activation of the adenosine A2A receptor, especially inflammatory or obstructive airways diseases. Pharmaceutical compositions that contain the compounds and a process for preparing the compounds are also described.

  式(I)化合物 或其立体异构体或药学上可接受的盐、 其中 W、R1、R2 和 R3 的含义如说明书所示，可用于治疗由腺苷 A2A 受体激活介导的疾病，特别是炎症性或阻塞性气道疾病。还描述了含有这些化合物的药物组合物和制备这些化合物的工艺。