methyl tricyclo[3.3.1.0(3,7)]nonane-3-carboxylate | 160943-32-8

• 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 tricyclo[3.3.1.0(3,7)]nonane-3-carboxylate
• 英文别名: Methyl tricyclo[3.3.1.03,7]nonane-3-carboxylate
• CAS: 160943-32-8
• 化学式: C₁₁H₁₆O₂
• 分子量: 180.247
• InChiKey: DLOJAHBPDAVAMX-UHFFFAOYSA-N

物化性质

• 沸点：
  229.5±8.0 °C(Predicted)
• 密度：
  1.169±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methyl tricyclo[3.3.1.0(3,7)]nonane-3-carboxylate 在 盐酸 、 尿素 作用下， 以 2-甲基四氢呋喃 、 乙醚 、 三氟乙酸 为溶剂， 反应 24.0h， 生成 (2-isopropyladamant-1-yl)amine hydrochloride
  参考文献：
  名称：

  Synthesis and Anti-influenza A Virus Activity of 2,2-Dialkylamantadines and Related Compounds

  摘要：

  The synthesis of several 2,2-dialkyladamantyl-1-amines through the combination of a Ritter reaction with a Wagner-Meerwein rearrangement from noradamantane alcohols is reported. Several of the novel amines displayed low micromolar activities against several H1N1 influenza virus strains, including the amantadine-resistant A/PuertoRico/8/34 strain. Most of the compounds did not show cytotoxicity for MDCK cells.

  DOI：

  10.1021/ml300279b
• 作为产物：
  描述：

  1-acetyl noradamantane 在 sodium hypobromide 、 硫酸 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 3.33h， 生成 methyl tricyclo[3.3.1.0(3,7)]nonane-3-carboxylate
  参考文献：
  名称：

  [EN] HISTONE DEACETYLASE INHIBITORS FOR THE TREATMENT OF FUNGAL INFECTIONS
  [FR] INHIBITEURS D'HISTONE DÉACÉTYLASE POUR LE TRAITEMENT D'INFECTIONS FONGIQUES

  摘要：

  描述了式(I)的桥联化合物，它们的类似物、互变异构体、立体异构体、几何异构体、多晶形态、水合物、溶剂合物、药学上可接受的盐、药物组合物、代谢产物和其前药。该发明涉及用于治疗真菌感染的组合物和方法。这些化合物是选择性HDAC抑制剂，可作为固有的抗真菌化合物或增强其他抗真菌化合物（如唑类药物）的活性。

  公开号：

  WO2011058582A1

文献信息

• Carbon Tunneling in the Ring Expansion of Noradamantylchlorocarbene
  作者：Robert A. Moss、Ronald R. Sauers、Robert S. Sheridan、Jingzhi Tian、Peter S. Zuev

  DOI：10.1021/ja0488939

  日期：2004.8.1

  in solution with laser flash photolysis via its pyridinium ylide, and in N2 or Ar matrixes at 9 K with IR and UV/vis spectroscopy. At ambient temperatures, or on irradiation in the cryogenic matrixes, the carbene rearranged to 2-chloro-1-adamantene, which could be trapped in solution and which was characterized by IR and UV/vis at low temperatures. In the dark at 9 K, the carbene also slowly ring-expanded

  辐照 3-(3-noradamantyl)-3-chlorodiazirine 产生相应的去甲金刚烷基氯卡宾，可通过其吡啶鎓叶立德在溶液中用激光闪光光解检测到，在 N2 或 Ar 基质中在 9 K 下用红外和紫外/可见光谱检测。在环境温度下，或在低温基质中照射时，卡宾重排为 2-氯-1-金刚烷，其可以被困在溶液中，并在低温下通过 IR 和 UV/vis 进行表征。在 9 K 的黑暗中，卡宾也以大约 10 的速率缓慢环膨胀为氯金刚烷。比其 B3LYP 计算的激活屏障预测的快 10111 倍。提出低温重排是通过碳量子力学隧穿发生的。
• Xanthine derivatives
  申请人：KYOWA HAKKO KOGYO CO., LTD.

  公开号：EP0619316A1

  公开（公告）日：1994-10-12

  There is provided a novel xanthine Compound(I) wherein R¹ and R² are the same or different and each represent hydroxy-substituted, oxo-substituted or unsubstituted lower alkyl, Y is a single bond or alkylene, and Q is wherein R³ and R⁴ are the same or different and each represent hydrogen or hydroxy, n is 0 or 1; provided that when both of R³ and R⁴ are hydrogen, at least one of R¹ and R² is hydroxy-substituted or oxo-substituted lower alkyl; or a pharmaceutically acceptable salt thereof. The xanthine compound has adenosine A₁ receptor antagonizing activity, and thus shows diuretic effect, renal-protecting effect, bronchodilatory effect, cerebral function improving effect and anti-dementia effect.

  提供了一种新型黄嘌呤化合物(I) 其中 R¹ 和 R² 相同或不同，各自代表羟基取代、氧代取代或未取代的低级烷基，Y 为单键或亚烷基，Q 为 其中 R³ 和 R⁴ 相同或不同且各自代表氢或羟基，n 为 0 或 1；但当 R³ 和 R⁴ 均为氢时，R¹ 和 R² 中至少有一个是羟基取代的或氧化取代的低级烷基；或其药学上可接受的盐。 黄嘌呤化合物具有腺苷 A₁受体拮抗活性，因此具有利尿作用、肾保护作用、支气管扩张作用、脑功能改善作用和抗痴呆作用。
• Solvolyses of 2-Oxo Bridgehead Compounds:  A Critical Examination of π-Conjugative Stabilization of α-Carbonyl Carbocations
  作者：Ken'ichi Takeuchi、Yasushi Ohga、Masayasu Yoshida、Keizo Ikai、Tadashi Shibata、Midori Kato、Akio Tsugeno

  DOI：10.1021/jo970454n

  日期：1997.8.1

  The methodology of changing ring flexibility to detect the pi-conjugative stabilization of bridgehead carbocations has been applied to eight 2-oxo (X = O) bridgehead carbocations. On the basis of the solvolytic behavior observed in kinetics and product analyses, the eight 2-oxo bridgehead substrates were classified into three categories: three substrates solvolyzing without ion-pair return that leads to primary isomers (class A), three substrates that form primary isomers by ion-pair return during solvolysis (class B), and two substrates that undergo solvent addition to the carbonyl group to form hemiacetals during solvolysis (class C). It was concluded that the substrates of class C could not be used for the present purpose. Essentially constant ethanolysis rate ratios, k(X = O)/k(X = H-2), of 10(-8.2)-10(-8.7) at 25 degrees C were obtained between four 2-oxo substrates in classes A and B and the corresponding parent unsubstituted ones. The result was interpreted to suggest that the pi-conjugative stabilization of tertiary alpha-carbonyl carbocations is negligibly small, if present. Slightly more negative k(X = O)/k(X = H-2) values of 10(-9.7) and 10(-9.2) for highly flexible bicyclo[4.2.2]dec-1-yl and bicyclo[4.3.1]dec-l-yl systems, respectively, were attributed to complex conformations in the ground and incipient carbocations. PM3 calculations on some 2-methylene and 2-oxo bridgehead carbocations supported the experimental results. Comparison of the solvolysis rates of 1,1,3,3-tetramethyl-2-oxobutyl mesylate with those of 1,1,3,3-tetramethylbutyl mesylate estimated from the rates of the corresponding chloride also failed to support the pi-conjugative stabilization of alpha-carbonyl carbocations.
• Synthesis and Anti-influenza A Virus Activity of 2,2-Dialkylamantadines and Related Compounds
  作者：Eva Torres、Roser Fernández、Stéphanie Miquet、Mercè Font-Bardia、Evelien Vanderlinden、Lieve Naesens、Santiago Vázquez

  DOI：10.1021/ml300279b

  日期：2012.12.13

  The synthesis of several 2,2-dialkyladamantyl-1-amines through the combination of a Ritter reaction with a Wagner-Meerwein rearrangement from noradamantane alcohols is reported. Several of the novel amines displayed low micromolar activities against several H1N1 influenza virus strains, including the amantadine-resistant A/PuertoRico/8/34 strain. Most of the compounds did not show cytotoxicity for MDCK cells.
• [EN] HISTONE DEACETYLASE INHIBITORS FOR THE TREATMENT OF FUNGAL INFECTIONS<br/>[FR] INHIBITEURS D'HISTONE DÉACÉTYLASE POUR LE TRAITEMENT D'INFECTIONS FONGIQUES
  申请人：ORCHID RES LAB LTD

  公开号：WO2011058582A1

  公开（公告）日：2011-05-19

  Described are bridged compounds of the formula (I), their analogs, tautomeric forms, stereoisomers, geometrical isomers, polymorphs, hydrates, solvates, pharmaceutically acceptable salts, pharmaceutical compositions, metabolites and prodrugs thereof. The invention relates to compositions and methods to treat fungal infection. These compounds are selective HDAC inhibitors that act as inherent antifungal compounds or enhance the activity of other antifungal compounds such as azoles.

  描述了式(I)的桥联化合物，它们的类似物、互变异构体、立体异构体、几何异构体、多晶形态、水合物、溶剂合物、药学上可接受的盐、药物组合物、代谢产物和其前药。该发明涉及用于治疗真菌感染的组合物和方法。这些化合物是选择性HDAC抑制剂，可作为固有的抗真菌化合物或增强其他抗真菌化合物（如唑类药物）的活性。