cyclohexyl azidoacetate | 114703-78-5

• 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: cyclohexyl azidoacetate
• 英文别名: Cyclohexyl 2-azidoacetate
• CAS: 114703-78-5
• 化学式: C₈H₁₃N₃O₂
• 分子量: 183.21
• InChiKey: JHZXIYXMVLHWOH-UHFFFAOYSA-N

物化性质

• 沸点：
  85-90 °C(Press: 0.1 Torr)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  40.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  cyclohexyl azidoacetate 生成 glycine cyclohexyl ester
  参考文献：
  名称：

  VENUTI, MICHAEL C.;ALVAREZ, ROBERT;BRUNO, JOHN J.;STROSBERG, ARTHUR M.;GU+, J. MED. CHEM., 31,(1988) N 11, C. 2145-2152

  摘要：

  DOI：
• 作为产物：
  描述：

  2-溴乙酸环己基酯 在 sodium azide 作用下， 以 二甲基亚砜 为溶剂， 反应 3.0h， 以61%的产率得到cyclohexyl azidoacetate
  参考文献：
  名称：

  Design and synthesis of isatin/triazole conjugates that induce apoptosis and inhibit migration of MGC-803 cells

  摘要：

  A series of new isatin/triazole conjugates were designed based on the hypothesis that the ester-linked compounds could be enzymatically hydrolyzed by cellular esterases inside the cells. These compounds showed moderate to good growth inhibition toward the tested cancer cells, exerted selective inhibition toward MGC-803 cells and were less toxic to normal cells HL-7702 and GES-1. Of these compounds, compound 5a showed the best inhibitory activity against MGC-803 cells (IC50 = 9.78 mu M), induced apoptosis through multiple mechanisms, as well as inhibited migration of MGC-803 cells. (C) 2016 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2016.08.065

文献信息

• “On Water” Direct Catalytic Vinylogous Aldol Reaction of Silyl Glyoxylates
  作者：Hong Pan、Man-Yi Han、Pinhua Li、Lei Wang

  DOI：10.1021/acs.joc.9b01945

  日期：2019.11.1

  The unique reactivity of water in the direct catalytic vinylogous aldol reaction of silyl glyoxylates is reported. With the hydrogen-bonding networks from water, the unfavorable homogeneous reactions in organic solvents were severely suppressed, and the "on water" relay chemistry for the vinylogous aldol reaction was realized in heterogeneous conditions (water as solvent), providing the desired α-hydroxysilanes

  据报道，在乙醛酸甲硅烷基酯的直接催化乙烯基醇醛醇醛反应中，水具有独特的反应性。通过水与氢的键合网络，可以严重抑制有机溶剂中不利的均相反应，并且在非均相条件下（水为溶剂）实现了乙烯基醇醛醇缩醛反应的“水上”中继化学反应，从而提供了所需的α-羟基硅烷具有高产的季碳中心。此外，还展示了对水在生物系统中作用的新见解。
• Inhibitors of cyclic AMP phosphodiesterase. 4. Synthesis and evaluation of potential prodrugs of lixazinone (N-cyclohexyl-N-methyl-4-[(1,2,3,5-tetrahydro-2-oxoimidazo[2,1-b]quinazolin-7-yl)oxy]butyramide, RS-82856)
  作者：Michael C. Venuti、Robert Alvarez、John J. Bruno、Arthur M. Strosberg、Leo Gu、Hi Shi Chiang、Ian J. Massey、Nancy Chu、John H. Fried

  DOI：10.1021/jm00119a015

  日期：1988.11

  The cyclic AMP phosphodiesterase (cAMP PDE) inhibitor and cardiotonic agent lixazinone (N-cyclohexyl-N-methyl-4-[(1,2,3,5-tetrahydro-2- oxoimidazo[2,1-b]quinazolin-7-yl)oxy]butyramide, RS-82856, 1) and its acid and base addition salts were found to be insufficiently soluble in formulations suitable for intravenous administration. These results prompted an investigation into potential prodrugs with

  环状AMP磷酸二酯酶（cAMP PDE）抑制剂和强心药lixazinone（N-环己基-N-甲基-4-[（1,2,3,5-四氢-2-氧代咪唑[2,1-b]喹唑啉-7-发现）））氧基]丁酰胺，RS-82856，1）及其酸和碱加成盐在适用于静脉内给药的制剂中溶解性不足。这些结果促使人们对具有提高的水溶性的潜在前药进行了研究，旨在通过三种不同的机制释放1：（1）α-羧酰胺的脱羧；（2）可溶的N-1-（酰氧基）甲基或（N，N-二烷基氨基）甲基部分的水解损失；或（3）胍基酯或酰胺的分子内封闭。通过三个标准对目标化合物作为1的传输系统进行了评估：（1）在生理条件下化学转化率为1；（2）在固定时间点抑制IV型cAMP PDE；（3）通过静脉内和口服给予的麻醉犬体内的变力活性。发现从4a（系列1）释放1太慢，以至于不能作为1的前药使用，因为脱羧只能由强酸诱导，而在强酸条件下发现水解开环剧烈竞争。相反，尽管
• N-N-disubstituted-omega-(2-amino-3-(carbonylmethyl)-3,4-dihydroquinazolinyl) oxyalkylamides and related compounds
  申请人：SYNTEX (U.S.A.) INC.

  公开号：EP0254327A2

  公开（公告）日：1988-01-27

  Pharmaceutical compositions comprising, or compositions consisting essentially of, compounds according to the formula or an optical isomer thereof wherein Z is oxygen or NR²; n is an integer of 1 to 6; R¹ and R² are independently hydrogen; alkyl of 1 to 12 carbon atoms; cycloalkyl of 3 to 12 carbon atoms; hydroxalkyl of 1 to 6 carbon atoms; cycloalkyl lower alkyl of 4 to 12 carbon atoms wherein the cycloalkyl ring is optionally substituted with a lower alkyl, lower alkoxy, -OH, -OCOR³, halo, -N(R³)₂, -NHCOR³, -COOH, or -COOR³ group wherein R³ is lower alkyl; and phenyl or phenyl lower alkyl wherein phenyl is optionally substituted with at least one lower alkyl, halo or lower alkoxy group or an -N(R³)₂, -NHCOR³, -COOH, or -COOR³ group wherein R³ is lower alkyl; or R¹ and R² are combined with the N to which they are attached to form a cyclic secondary amine radical having from 5 to 8 atoms, where, in addition to the N atom, the atoms in the radical comprise carbon atoms and can include one oxygen or sulfur atom, or one optionally lower alkyl substituted nitrogen atom; HX is optionally present and when present represents the acid portion of a pharmaceutically acceptable acid additional salt; A is NR⁴R⁵ wherein R⁴ and R⁵ are independently selected from the group consisting of: hydrogen; alkyl of 1 to 6 carbon atoms; hydroxyalkyl of 2 to 6 carbon atoms; cycloalkyl of 3 to 8 carbon atoms or cycloalkyl lower alkyl of 4 to 12 carbon atoms wherein the cycloalkyl ring is optionally substituted with a lower alkyl, lower alkoxy, -OH, -OCOR³, halo, -N(R³)₂, -NHCOR³, -COOH, or -COOR³ group wherein R³ is lower alkyl; and phenyl or phenyl lower alkyl wherein phenyl is optionally substituted with at least one lower alkyl, halo or lower alkoxy group or an -N(R³)₂, -NHCOR³, -COOH, or -COOR³ group wherein R³ is lower alkyl; or wherein R⁴ and R⁵ are combined to form a compound selected from the group consisting of: morpholinyl, piperidinyl, perhexylenyl, N-loweralkylpiperazinyl, pyrrolidinyl, tetrahydroquinolinyl, tetrahydroisoquinolinyl, (±)-decahydroquinolinyl and indolinyl. The invention is also directed to certain compounds of the above class. The compounds of Formula I are cyclic AMP phosphodiesterase inhibitors useful as antithrombotic and inotropic agents and the like in mammals.

  药物组合物，包含或主要包含如下式的化合物 或其光学异构体 其中 Z 是氧或 NR² n 是 1 至 6 的整数； R¹ 和 R² 独立地为氢；1 至 12 个碳原子的烷基；3 至 12 个碳原子的环烷基；1 至 6 个碳原子的羟烷基；4 至 12 个碳原子的环烷基低级烷基，其中环烷基环任选被低级烷基、低级烷氧基、-OH、-OCOR³、卤代、-N(R³)₂、-NHCOR³、-COOH 或 -COOR³ 基团取代，其中 R³ 为低级烷基；苯基或苯基低级烷基，其中苯基可选择被至少一个低级烷基、卤代或低级烷氧基或-N(R³)₂、-NHCOR³、-COOH 或-COOR³基团取代，其中 R³ 为低级烷基；或 R¹ 和 R² 与它们所连接的 N 结合，形成具有 5 至 8 个原子的环状仲胺基，其中，除 N 原子外，基中的原子包括碳原子，还可包括一个氧原子或硫原子，或一个任选被低级烷基取代的氮原子； HX 可任选存在，存在时代表药学上可接受的酸附加盐的酸部分； A 是 NR⁴R⁵，其中 R⁴ 和 R⁵ 独立选自由以下组成的组：氢；1 至 6 个碳原子的烷基；2 至 6 个碳原子的羟烷基；3 至 8 个碳原子的环烷基或 4 至 12 个碳原子的环烷基低级烷基，其中环烷基环任选被低级烷基、低级烷氧基、-OH、-OCOR³、卤代、-N(R³)₂、-NHCOR³、-COOH 或 -COOR³ 基团取代，其中 R³ 为低级烷基；苯基或苯基低级烷基，其中苯基任选被至少一个低级烷基、卤代或低级烷氧基或-N(R³)₂、-NHCOR³、-COOH 或-COOR³基团取代，其中 R³ 为低级烷基；或其中 R⁴ 和 R⁵ 结合形成选自由以下组成的化合物：吗啉基、哌啶基、过己烯基、N-低烷基哌嗪基、吡咯烷基、四氢喹啉基、四氢异喹啉基、(±)-十氢喹啉基和吲哚啉基。本发明还涉及上述类别中的某些化合物。式 I 的化合物是环 AMP 磷酸二酯酶抑制剂，可用作哺乳动物的抗血栓和肌力促进剂等。
• VENUTI, MICHAEL C.
  作者：VENUTI, MICHAEL C.

  DOI：——

  日期：——
• VENUTI, MICHAEL C.;ALVAREZ, ROBERT;BRUNO, JOHN J.;STROSBERG, ARTHUR M.;GU+, J. MED. CHEM., 31,(1988) N 11, C. 2145-2152
  作者：VENUTI, MICHAEL C.、ALVAREZ, ROBERT、BRUNO, JOHN J.、STROSBERG, ARTHUR M.、GU+

  DOI：——

  日期：——