(+/-)-methyl cis-3-(chloromethanoyl)cyclopentanecarboxylate | 85174-63-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (+/-)-methyl cis-3-(chloromethanoyl)cyclopentanecarboxylate
• 英文别名: (+/-)-cis-1-chlorocarbonyl-cyclopentane-carboxylic acid-(3)-methyl ester；(+/-)-cis-1-Chlorcarbonyl-cyclopentan-carbonsaeure-(3)-methylester；methyl (1S,3R)-3-carbonochloridoylcyclopentane-1-carboxylate
• CAS: 85174-63-6；116595-44-9；116940-83-1
• 化学式: C₈H₁₁ClO₃
• 分子量: 190.627
• InChiKey: TYWZGOWRMWCWFP-RITPCOANSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+/-)-methyl cis-3-(chloromethanoyl)cyclopentanecarboxylate 在 lithium aluminium tetrahydride 、 N,N-二甲基苯胺 作用下， 以 四氢呋喃 为溶剂， 生成 cis-tert-butyl 3-(hydroxymethyl)cyclopentanecarboxylate
  参考文献：
  名称：

  Reaction pathways of 3-(3'-methylenecyclobutyl)propyl and 2-(3'-methylenecyclobutyl)ethyl radicals

  摘要：

  DOI：

  10.1021/jo00281a043
• 作为产物：
  描述：

  (1R,3S)-dimethyl cyclopentane-1,3-dicarboxylate 在 barium dihydroxide 、 氯化亚砜 、 水 作用下， 生成 (+/-)-methyl cis-3-(chloromethanoyl)cyclopentanecarboxylate
  参考文献：
  名称：

  Reaction pathways of 3-(3'-methylenecyclobutyl)propyl and 2-(3'-methylenecyclobutyl)ethyl radicals

  摘要：

  DOI：

  10.1021/jo00281a043

文献信息

• Synthesis of cyclopentane analogs of 1-(2′,3′-dideoxy-β-<i>glycero</i>-pentofuranosyl)pyrimidine nucleosides
  作者：Lucjan J. J. Hronowski、Walter A. Szarek

  DOI：10.1139/v88-009

  日期：1988.1.1

  Synthesis of new carbocyclic analogs of 1-(2′,3′-dideoxy-glycero-pentofuranosyl)pyrimidine nucleosides having the uracil (34), 2-thiouracil (33), 2-thiothymine (31), cytosine (44), and 5-methylcytosine (43) bases is described. The nucleoside analogs having the uracil, 2-thiouracil, and 2-thiothymine bases were prepared by coupling cis-3-aminocyclopentanemethanol (8) with 3-ethoxypropenoyl isocyanate

  具有尿嘧啶 (34)、2-硫尿嘧啶 (33)、2-硫胸腺嘧啶 (31)、胞嘧啶 (44) 和 1-(2',3'-二脱氧-甘油-戊呋喃糖基) 嘧啶核苷的新碳环类似物的合成描述了 5-甲基胞嘧啶 (43) 碱基。具有尿嘧啶、2-硫尿嘧啶和 2-硫胸腺嘧啶碱基的核苷类似物是通过将顺-3-氨基环戊烷甲醇 (8) 与 3-乙氧基丙烯酰基异氰酸酯 (26)、3-乙氧基丙烯酰基异硫氰酸酯 (25) 和 3-甲氧基- 2-甲基丙烯酰基异硫氰酸酯 (23) 分别得到相应的酰基脲 (30) 和酰基硫脲 (29 和 27)。酰基脲在 2 N H 2 SO 4 中环化，酰基硫脲在 15 N氨水中环化，得到相应的核苷类似物。通过4-氯嘧啶酮中间体（42和41）分别从尿嘧啶和胸腺嘧啶核苷类似物制备含有胞嘧啶（44）和5-甲基胞嘧啶（43）碱基的核苷类似物。降冰片烯合成顺式3-氨基环戊烷甲醇(8)...
• Novel 3,4-Isoxazolediamides as Potent Inhibitors of Chaperone Heat Shock Protein 90
  作者：Riccardo Baruchello、Daniele Simoni、Giuseppina Grisolia、Giuseppina Barbato、Paolo Marchetti、Riccardo Rondanin、Stefania Mangiola、Giuseppe Giannini、Tiziana Brunetti、Domenico Alloatti、Grazia Gallo、Andrea Ciacci、Loredana Vesci、Massimo Castorina、Ferdinando M. Milazzo、Maria L. Cervoni、Mario B. Guglielmi、Marcella Barbarino、Rosanna Foderà、Claudio Pisano、Walter Cabri

  DOI：10.1021/jm201155e

  日期：2011.12.22

  A structural investigation on the isoxazole scaffold led to the discovery of 3,4-isoxazolediamide compounds endowed with potent Hsp90 inhibitory properties. We have found that compounds possessing a nitrogen atom directly attached to the C-4 heterocycle ring possess in vitro Hsp90 inhibitory properties at least comparable to those of the structurally related 4,S-diarylisoxazole derivatives. A group of compounds from this series of diamides combine potent binding affinity and cell growth inhibitory activity in both series of alkyl- and aryl- or heteroarylarnides, with IC50 in the low nanomolar range. The 3,4-isoxazolediamides were also very effective in causing dramatic depletion of the examined client proteins and, as expected for the Hsp90 inhibitors, always induced a very strong increase in the expression levels of the chaperone Hsp70. In vivo studies against human epidermoid carcinoma A431 showed an antitumor effect of morpholine derivative 73 comparable to that induced by the reference compound 10.
• Exploring in vitro and in vivo Hsp90 inhibitors activity against human protozoan parasites
  作者：Giuseppe Giannini、Gianfranco Battistuzzi

  DOI：10.1016/j.bmcl.2014.12.048

  日期：2015.2

  A set of compounds, previously selected as potent Hsp90 alpha inhibitors, has been studied on a panel of human parasites. 5-Aryl-3,4-isoxazolediamide derivatives (1) were active against two protozoa, Trypanosoma brucei rhodesiense and Plasmodium falciparum, with a good tolerability toward cytotoxicity on non-malignant L6 rat myoblast cell line, unlike the 1,5-diaryl,4-carboxamides-1,2,3-triazole derivatives (2) which, while showing a single-digit nM range activity against the same protozoa, were also highly cytotoxic on L6 cells. In a subsequent in vivo study, two isoxazolediamide derivatives, 1a and 1b, were very efficacious on the sleeping sickness-causing agent with a clear parasitaemia during treatment. These data, however, showed that not all protozoa are sensitive to Hsp90 inhibitors, as well as not all Hsp90 inhibitors are equally active on parasites. (C) 2014 Elsevier Ltd. All rights reserved.
• Guha; Ranganathan, Chemische Berichte, 1936, vol. 69, p. 1195,1198
  作者：Guha、Ranganathan

  DOI：——

  日期：——
• Reaction pathways of 3-(3'-methylenecyclobutyl)propyl and 2-(3'-methylenecyclobutyl)ethyl radicals
  作者：Paul E. Pigou

  DOI：10.1021/jo00281a043

  日期：1989.9