2-(quinolin-8-ylamino)ethanol | 1335496-81-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2-(quinolin-8-ylamino)ethanol
• CAS: 1335496-81-5
• 化学式: C₁₁H₁₂N₂O
• 分子量: 188.229
• InChiKey: JPELKJKHWXFHFM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  45.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(quinolin-8-ylamino)ethanol 在 manganese (II) acetate tetrahydrate 作用下， 以 甲醇 为溶剂， 反应 8.0h， 生成 2-[[5-[8-(2-Hydroxyethylamino)quinolin-5-yl]quinolin-8-yl]amino]ethanol
  参考文献：
  名称：

  5,5'-联喹啉衍生物的螺旋自组装的酸包合性质

  摘要：

  为了理解阴离子在螺旋自组装折叠中的堆积，一种新的有机螺旋5,5'-联喹啉衍生物bis-5,5'-[2-（喹啉-8-基氨基）乙醇] ，通过锰（II）催化的CC键形成反应合成具有通过柔性亚乙基键连接的羟基侧基的化合物。该化合物采用螺旋结构，喹啉环的两个平面之间的二面角为60.08°，并借助羟基和喹啉环中的氮原子以及C–H··O相互作用自组装。bis-5,5'-[2-（quinolin-8-ylamino）ethanol]的螺旋自组装可以封装两种不同形状的客体，即三角形平面（硝酸盐）和四面体（高氯酸盐），而不会明显丢失其原始形状螺旋度。发现该螺旋分子与高氯酸和硝酸的相互作用在溶液中是相似的。但是，固态的高氯酸会形成盐，而硝酸会与其形成共晶。

  DOI：

  10.1021/cg201052k
• 作为产物：
  描述：

  methyl 2-(quinolin-8-ylamino)acetate 在 甲醇 、 sodium tetrahydroborate 作用下， 以 四氢呋喃 为溶剂， 以67%的产率得到2-(quinolin-8-ylamino)ethanol
  参考文献：
  名称：

  5,5'-联喹啉衍生物的螺旋自组装的酸包合性质

  摘要：

  为了理解阴离子在螺旋自组装折叠中的堆积，一种新的有机螺旋5,5'-联喹啉衍生物bis-5,5'-[2-（喹啉-8-基氨基）乙醇] ，通过锰（II）催化的CC键形成反应合成具有通过柔性亚乙基键连接的羟基侧基的化合物。该化合物采用螺旋结构，喹啉环的两个平面之间的二面角为60.08°，并借助羟基和喹啉环中的氮原子以及C–H··O相互作用自组装。bis-5,5'-[2-（quinolin-8-ylamino）ethanol]的螺旋自组装可以封装两种不同形状的客体，即三角形平面（硝酸盐）和四面体（高氯酸盐），而不会明显丢失其原始形状螺旋度。发现该螺旋分子与高氯酸和硝酸的相互作用在溶液中是相似的。但是，固态的高氯酸会形成盐，而硝酸会与其形成共晶。

  DOI：

  10.1021/cg201052k

文献信息

• [EN] NOVEL MOLECULES THAT SELECTIVELY INHIBIT HISTONE DEACETYLASE 6 RELATIVE TO HISTONE DEACETYLASE 1<br/>[FR] NOUVELLES MOLÉCULES QUI INHIBENT SÉLECTIVEMENT L'HISTONE-DÉACÉTYLASE 6 PAR RAPPORT À L'HISTONE-DÉACÉTYLASE 1
  申请人：UNIV COLUMBIA

  公开号：WO2013052110A1

  公开（公告）日：2013-04-11

  The compounds of the present invention are HDAC6 selective inhibitors which are identified on the basis of accumulation of acetylated tubulin without accumulation of acetylated histones. Histone deacetylase or "HDAC" refers to enzymes capable of cleaving an acetyl group (-C(=0)CH3) from proteins, including histone and microtubulins. Compositions comprising the molecules and methods for their use to inhibit the activity of histone deacetylase, including for treatment, are also disclosed.

  本发明的化合物是HDAC6选择性抑制剂，其基于乙酰化微管蛋白的积累而被识别，而不是乙酰化组蛋白的积累。组蛋白去乙酰化酶或“HDAC”指的是能够从蛋白质（包括组蛋白和微管蛋白）中切除乙酰基（-C(=0)CH3）的酶。还公开了包含这些分子的组合物以及用于抑制组蛋白去乙酰化酶活性的方法，包括用于治疗的方法。
• NOVEL MOLECULES THAT SELECTIVELY INHIBIT HISTONE DEACETYLASE 6 RELATIVE TO HISTONE DEACETYLASE 1
  申请人：The Trustees of Columbia University in the City of New York

  公开号：US20140288119A1

  公开（公告）日：2014-09-25

  This invention provides a compound having the structure: wherein R 1 is H, halogen, —NR 5 R 6 , —NR 5 —C(═O)—R 6 , —NH—C(═O)—OR 7 , —OR 7 , —NO 2 , —CN, —SR 7 , —SO 2 R 7 , —CO 2 R 7 , CF 3 , —SOR 7 , —POR 7 , —C(═S)R 7 , —C(═O)—NR 5 R 6 , —CH 2 —C(═O)—NR 5 R 6 , —C(═NR 5 )R 6 , —P(═O)(OR 5 )(OR 6 ), —P(OR 5 )(OR 6 ), —C(═S)R 7 , C 1-5 alkyl, C 2-5 alkenyl, C 2-5 alkynyl, aryl, heteroaryl, or heterocyclyl, wherein R 5 , R 6 , and R 7 and are each, independently, H, C 1-5 alkyl, C 2-5 alkenyl, C 2-5 alkynyl, heteroalkyl, cycloalkyl, heterocycloalkyl, aryl, or heteroaryl; m is an integer from 0 to 2; R 2 and R 3 are each, independently, H, halogen, —NH 2 , —CX 3 , —C(═O)OR 8 , C(═O)R 8 , —C(═O)NR 9 R 10 , C 1-10 alkyl, C 2-10 alkenyl, C 2-10 alkynyl, heteroalkyl, aryl, heteroaryl, or heterocyclyl; wherein X is Cl, Br, or F; R 8 , R 9 and R 10 are each, independently, H, C 1-5 alkyl, C 2-5 alkenyl, C 2-5 alkynyl, heteroalkyl, cycloalkyl, heterocycloalkyl, aryl, or heteroaryl; Q is —Ar 1 —Z— or —Z—Ar 1 —Z—, wherein Ar 1 is aryl or heteroaryl; and each occurrence of Z is independently present or absent, and when present is —O—, —S—, —CH 2 —, —C(O)— —NH—, —NH—NH—, —NHC(═O)—, —C(═O)NH—, —NHC(═O)CH 2 NH—, —NHC(═O)CH 2 C(═O)—, —N(OH)—, —CH 2 CH 2 — or —NHC(═O)CH═CH—; and R 4 is alkyl, —OR 11 or —NH—OR 11 , wherein R 11 is H, C 1-10 alkyl, C 2-10 alkenyl, C 2-10 alkynyl, aryl, heteroaryl, or heterocyclyl, and when Q is —Ar 1 —Z—, Z is absent, Ar 1 is phenyl, R 2 and R 3 are H, n=1, and R 4 is —NHOH, then R 1 is other than carbazole, tetrahydro-β-carboline, tetrahydro-γ-carboline, —C(═O)—NR 5 R 6 and —NR 5 —C(═O)—R 6 , wherein one of R 5 or R 6 is quinoline and the other of R 5 or R 6 is H; or a pharmaceutically acceptable salt thereof.

  该发明提供了一种具有以下结构的化合物：其中，R1为H、卤素、—NR5R6、—NR5—C(═O)—R6、—NH—C(═O)—OR7、—OR7、—NO2、—CN、—SR7、—SO2R7、—CO2R7、CF3、—SOR7、—POR7、—C(═S)R7、—C(═O)—NR5R6、—CH2—C(═O)—NR5R6、—C(═NR5)R6、—P(═O)(OR5)(OR6)、—P(OR5)(OR6)、—C(═S)R7、C1-5烷基、C2-5烯基、C2-5炔基、芳基、杂芳基或杂环烷基，其中，R5、R6和R7各自独立地为H、C1-5烷基、C2-5烯基、C2-5炔基、杂基、环烷基、杂环烷基、芳基或杂芳基；m为0到2的整数；R2和R3各自独立地为H、卤素、—NH2、—CX3、—C(═O)OR8、C(═O)R8、—C(═O)NR9R10、C1-10烷基、C2-10烯基、C2-10炔基、杂基、芳基、杂芳基或杂环烷基，其中，X为Cl、Br或F；R8、R9和R10各自独立地为H、C1-5烷基、C2-5烯基、C2-5炔基、杂基、环烷基、杂环烷基、芳基或杂芳基；Q为—Ar1—Z—或—Z—Ar1—Z—，其中，Ar1为芳基或杂芳基；Z的每次出现都是独立存在或缺失的，当存在时为—O—、—S—、—CH2—、—C(O)——NH—、—NH—NH—、—NHC(═O)—、—C(═O)NH—、—NHC(═O)CH2NH—、—NHC(═O)CH2C(═O)—、—N(OH)—、—CH2CH2—或—NHC(═O)CH═CH—；R4为烷基、—OR11或—NH—OR11，其中，R11为H、C1-10烷基、C2-10烯基、C2-10炔基、芳基、杂芳基或杂环烷基，当Q为—Ar1—Z—，Z不存在，Ar1为苯基，R2和R3为H，n=1，且R4为—NHOH时，R1不是咔唑、四氢-β-咔啉、四氢-γ-咔啉、—C(═O)—NR5R6和—NR5—C(═O)—R6，其中R5或R6之一为喹啉，另一个为H；或其药学上可接受的盐。
• NOVEL MOLECULES THAT SELECTIVELY INHIBIT HISTONE DEACETYLASE 6 RELATIVE TO HISTONE DEACETYLASE
  申请人：Breslow Ronald

  公开号：US20170066712A1

  公开（公告）日：2017-03-09

  This invention provides a compound having the structure: wherein R 1 is H, halogen, —NR 5 R 6 , —NR 5 —C(═0)-R 6 , —NH—C(═O)—OR 7 , —OR 7 , —NO 2 , —CN, —SR 7 , —SO 2 R 7 , —CO 2 R 7 , CF 3 , —SOR 7 , —POR 7 , —C(═S)R 7 , —C(═O)—NR 5 R 6 , —CH 2 —C(═O)—NR 5 R 6 , —C(═NR 5 )R 6 , —P(═O)(OR 5 )(OR 6 ), —P(OR 5 )(OR 6 ), —C(═S)R 7 , C 1-5 alkyl, C 2-5 alkenyl, C 2-5 alkynyl, aryl, heteroaryl, or heterocyclyl, wherein R 5 , R 6 , and R 7 and are each, independently, H, C 1-5 alkyl, C 2-5 alkenyl, C 2-5 alkynyl, heteroalkyl, cycloalkyl, heterocycloalkyl, aryl, or heteroaryl; m is an integer from 0 to 2; R 2 and R 3 are each, independently, H, halogen, —NH 2 , —CX 3 , —C(═O)OR 8 , C(═O)R 8 , —C(═O)NR 9 R 10 , C 1-10 alkyl, C 2-10 alkenyl, C 2-10 alkynyl, heteroalkyl, aryl, heteroaryl, or heterocyclyl; wherein X is Cl, Br, or F; R 8 , R 9 and R 10 are each, independently, H, C 1-5 alkyl, C 2-5 alkenyl, C 2-5 alkynyl, heteroalkyl, cycloalkyl, heterocycloalkyl, aryl, or heteroaryl; Q is —Ar 1 —Z— or —Z—Ar 1 —Z—, wherein Ar 1 is aryl or heteroaryl; and each occurrence of Z is independently present or absent, and when present is —O—, —S—, —CH 2 —, —C(O)—, —NH—, —NH—NH—, —NHC(═O)—, —C(═O)NH—, —NHC(═O)CH 2 NH—, —NHC(═O)CH 2 C(═O)—, —N(OH)—, —CH 2 CH 2 — or —NHC(═O)CH═CH—; and R 4 is alkyl, —OR 11 or —NH—OR 11 , wherein R 11 is H, C 1-10 alkyl, C 2-10 alkenyl, C 2-10 alkynyl, aryl, heteroaryl, or heterocyclyl, and when Q is —Ar 1 —Z—, Z is absent, Ar 1 is phenyl, R 2 and R 3 are H, n=1, and R 4 is —NHOH, then R 1 is other than carbazole, tetrahydro-β-carboline, tetrahydro-γ-carboline, —C(═O)—NR 5 R 6 and —NR 5 —C(═0)-R 6 , wherein one of R 5 or R 6 is quinline and the other of R 5 or R 6 is H; or a pharmaceutically acceptable salt thereof.
• US9499479B2
  申请人：——

  公开号：US9499479B2

  公开（公告）日：2016-11-22
• Acid Inclusion Properties of Helical Self-Assembly of a 5,5′-Biquinoline Derivative
  作者：Dipjyoti Kalita、Jubaraj B. Baruah

  DOI：10.1021/cg201052k

  日期：2011.11.2

  structure with a dihedral angle between two planes of quinoline rings as 60.08° and self-assembles with the aid of hydoxy groups and nitrogen atoms in the quinoline rings along with C–H···O interactions. The helical self-assembly of bis-5,5′-[2-(quinolin-8-ylamino)ethanol] can encapsulate guests of two different shapes, namely trigonal planar (nitrate) and tetrahedral (perchlorate), without significantly

  为了理解阴离子在螺旋自组装折叠中的堆积，一种新的有机螺旋5,5'-联喹啉衍生物bis-5,5'-[2-（喹啉-8-基氨基）乙醇] ，通过锰（II）催化的CC键形成反应合成具有通过柔性亚乙基键连接的羟基侧基的化合物。该化合物采用螺旋结构，喹啉环的两个平面之间的二面角为60.08°，并借助羟基和喹啉环中的氮原子以及C–H··O相互作用自组装。bis-5,5'-[2-（quinolin-8-ylamino）ethanol]的螺旋自组装可以封装两种不同形状的客体，即三角形平面（硝酸盐）和四面体（高氯酸盐），而不会明显丢失其原始形状螺旋度。发现该螺旋分子与高氯酸和硝酸的相互作用在溶液中是相似的。但是，固态的高氯酸会形成盐，而硝酸会与其形成共晶。