methyl c-3,c-4-isopropylidenedioxy-r-1-cyclopentanecarboxylate | 77714-60-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl c-3,c-4-isopropylidenedioxy-r-1-cyclopentanecarboxylate
• 英文别名: methyl (3aR,5r,6aS)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxole-5-carboxylate
• CAS: 77714-60-4
• 化学式: C₁₀H₁₆O₄
• 分子量: 200.235
• InChiKey: OYZNSQPDZQIHRG-RNLVFQAGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.09
• 重原子数：
  14.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  methyl c-3,c-4-isopropylidenedioxy-r-1-cyclopentanecarboxylate 生成 methyl (3aR,5s,6aS)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxole-5-carboxylate
  参考文献：
  名称：

  RASTETTER, W. H.;PHILLION, D. P., J. ORG. CHEM., 1981, 46, N 16, 3204-3208

  摘要：

  DOI：
• 作为产物：
  描述：

  methyl (1S,2R,3S,4S)-2-benzoyloxy-3,4-isopropylidenedioxycyclopentane-1-carboxylate 在 palladium on activated charcoal 、 氢气 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 反应 16.5h， 生成 methyl c-3,c-4-isopropylidenedioxy-r-1-cyclopentanecarboxylate
  参考文献：
  名称：

  Highly Substituted Cyclopentane–CMP Conjugates as Potent Sialyltransferase Inhibitors

  摘要：

  Sialylconjugates on cell surfaces are involved in many biological events such as cellular recognition, signal transduction, and immune response. It has been reported that aberrant sialylation at the nonreducing end of glycoconjugates and overexpression of sialyltransferases (STs) in cells are correlated with the malignance, invasion, and metastasis of tumors. Therefore, inhibitors of STs would provide valuable leads for the discovery of antitumor drugs. On the basis of the transition state of the enzyme-catalyzed sialylation reaction, we proposed that the cydopentane skeleton in its two puckered conformations might mimic the planar structure of the donor (CMP-Neu5Ac) in the transition state. A series of cydopentane-containing compounds were designed and synthesized by coupling different cydopentane alpha-hydroxyphosphonates with cytidine phosphoramidite. Their inhibitory activities against recombinant human ST6Gal-I were assayed, and a potent inhibitor 481 with a K-i of 0.028 +/- 0.006 mu M was identified. The results show that the cydopentanoid-type compounds could become a new type of sialyltransferase inhibitors as biological probes or drug leads.

  DOI：

  10.1021/acs.jmedchem.5b01181

文献信息

• DIURETICS
  申请人：ALI Amjad

  公开号：US20100029678A1

  公开（公告）日：2010-02-04

  A compound having the structure wherein X is selected from the group consisting of: a bond, —NHCH 2 (CH 2 ) n CH 2 OC(O)—, —CH 2 NHC(O)CH 2 NHC(O)—, —CH 2 OC(O)—, —OCH(CH 3 )OC(O)—, —OCH 2 OC(O)—, —O—, —NR 1 —, —CR 1 R 3 —, —(CH 2 ) p —, —(CH 2 ) q NR 1 C(O)—, —CHR 5 NR 2 C(O)—, —(CH 2 ) q C(O)—, —(CH 2 ) q C(O)—, —(CH 2 ) q C(O)NR 1 —, or a pharmaceutically acceptable salt thereof, and methods of using the compounds for treating, hypertension.

  具有以下结构的化合物： 其中 X 是从以下组中选择： 一个键，—NHCH 2 (CH 2 ) n CH 2 OC(O)—, —CH 2 NHC(O)CH 2 NHC(O)—, —CH 2 OC(O)—, —OCH(CH 3 )OC(O)—, —OCH 2 OC(O)—, —O—, —NR 1 —, —CR 1 R 3 —, —(CH 2 ) p —, —(CH 2 ) q NR 1 C(O)—, —CHR 5 NR 2 C(O)—, —(CH 2 ) q C(O)—, —(CH 2 ) q C(O)—, —(CH 2 ) q C(O)NR 1 —， 或其药物可接受的盐，以及使用这些化合物治疗高血压的方法。
• Syntheses of four thiol-substituted crown ethers
  作者：William H. Rastetter、Dennis P. Phillion

  DOI：10.1021/jo00329a011

  日期：1981.7
• MCMURRY, JOHN E.;DUSHIN, RUSSELL G., J. AMER. CHEM. SOC., 112,(1990) N9, C. 6942-6949
  作者：MCMURRY, JOHN E.、DUSHIN, RUSSELL G.

  DOI：——

  日期：——
• ANTIMICROBIAL AGENTS
  申请人：THE UNIVERSITY OF WARWICK

  公开号：US20200048183A1

  公开（公告）日：2020-02-13

  The invention provides novel analogues of enacyloxin Ha and their pharmaceutically acceptable salts, metabolites, isomers (e.g. stereoisomers) and prodrugs. Such compounds are effective in the treatment of infections caused by Gram-negative bacteria such as Acinetobacter baumannii . Compounds in accordance with the invention include those of formula (A), and their pharmaceutically acceptable salts, metabolites, isomers (e.g. stereoisomers) and prodrugs: In formula (A): X is 0 or NR x (where R* is either H or C 1-3 alkyl, e.g. CH 3 ); R 1 is a 5- or 6-membered, saturated or unsaturated, carbocyclic ring optionally substituted by one or more substituents, or R 1 is an optionally substituted straight-chained or branched C 1-6 alkyl group (e.g. C 1-3 alkyl group); R 2 is H, F, Cl, Br, I or CH 3 ; R 3 is H or OH; R 8 is a straight-chained or branched C 1-8 alkyl group (e.g. a C 1-6 alkyl group); Y is one of the following groups: (wherein each * denotes the point of attachment of the group to the remainder of the molecule; R 9 is H, F, Cl, Br or I; R 4 and R 5 are independently selected from H and OH, or R 4 and R 5 together are =0, preferably R 4 is H and R 5 is OH; R 6 is H, F, Cl, Br, I or CH 3 ; R 7 is H and R 7′ is OH, or R 7 and R 7′ together are =0, preferably R7 is H and R7′ is OH); and each — independently represents an optional bond (i.e. each of C 2 -C 3 , C 4 -C 5 , C 6 -C 7 , C 8 -C 9 and C 10 -C 11 are independently either C—C (single) or C═C (double) bonds).