2-(morpholin-4-yl)-5-methylaniline | 91429-92-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: 2-(morpholin-4-yl)-5-methylaniline
• 英文别名: N-(2-Amino-4-tolyl)-morpholin；5-methyl-2-morpholin-4-yl-aniline；4-(2-amino-4-methylphenyl)morpholine；5-methyl-2-(4-morpholinyl)aniline；5-Methyl-2-(morpholin-4-yl)aniline；5-methyl-2-morpholin-4-ylaniline
• CAS: 91429-92-4
• 化学式: C₁₁H₁₆N₂O
• mdl: MFCD09755879
• 分子量: 192.261
• InChiKey: FABHEYAZAOCBCH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.454
• 拓扑面积：
  38.5
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  2-(morpholin-4-yl)-5-methylaniline 以 1,4-二氧六环 、 水 为溶剂， 生成 5-methyl-2-morpholinophenyl isothiocyanate
  参考文献：
  名称：

  Phenylamidine and phenylguanidine derivatives and their use as

  摘要：

  公式I的化合物及其盐，其中n=0或1，R.sub.1和R.sub.2分别为脂肪族或环烷基，或NR.sub.1 R.sub.2是一个可选择取代的杂环环，R.sub.3是烷基，环烷基或可选择取代的氨基，R.sub.5是脂肪基，R.sub.6是H，可选择取代的脂肪基或环烷基，或R.sub.3和R.sub.5与它们连接的氮和碳原子形成一个可选择取代的杂环环，或R.sub.5和R.sub.6与它们连接的氮形成一个可选择取代的杂环环，R.sub.7是可选择取代的烷基，烷氧基，烷基硫醇，烷基磺醇，烷基磺酰基，烷氧羰基，三氟甲基或氰基，具有降血糖剂的用途。

  公开号：

  US05223498A1
• 作为产物：
  描述：

  3-硝基-4-氯甲苯 在 铁粉 、 氯化铵 作用下， 生成 2-(morpholin-4-yl)-5-methylaniline
  参考文献：
  名称：

  Benzimidazole Syntheses by Oxidative Cyclization with Peroxytrifluoroacetic Acid

  摘要：

  DOI：

  10.1021/ja01477a038

文献信息

• [EN] DIKETOPIPERAZINE DERIVATIVES AS P2X7 MODULATORS<br/>[FR] DÉRIVÉS DE DICÉTOPIPÉRAZINE COMME MODULATEURS DE P2X7
  申请人：GLAXO GROUP LTD

  公开号：WO2010125103A1

  公开（公告）日：2010-11-04

  The invention provides a compound of formula (I) or a pharmaceutically acceptable salt thereof: (I) wherein: A represents an aryl, heteroaryl or heterocyclyl group; and any ring or ring system of said aryl or heteroaryl is optionally substituted with 1 to 3 substituents, which may be the same or different, selected from the group consisting of halogen, C1-6 alkyl, -CF3, - OCF3, cyano, C1-6 alkoxy, -NR10R11, -X-aryl, -X-heteroaryl and -X-heterocyclyl; R1, R2, R3, R4 and R5 independently represent hydrogen, fluorine, chlorine, -CF3, cyano or C1-6 alkyl, such that at least one of R1, R2, R3, R4 and R5 is other than hydrogen; R6, R7, R8, R9, R10 and R11 independently represent hydrogen or C1-6 alkyl; X represents a linker selected from a bond, -(CH2)n- and -O-(CH2)n-; and n represents an integer from 1 to 3. The compounds or salts modulate P2X7 receptor function and are capable of antagonizing the effects of ATP at the P2X7 receptor ("P2X7 receptor antagonists").

  本发明提供了一种式(I)化合物或其药学上可接受的盐：(I)其中：A代表芳基、杂芳基或杂环基团；上述芳基或杂芳基的任何环或环系可选地被1至3个取代基取代，这些取代基可以相同或不同，选自卤素、C1-6烷基、-CF3、-OCF3、氰基、C1-6烷氧基、-NR10R11、-X-芳基、-X-杂芳基和-X-杂环基；R1、R2、R3、R4和R5各自独立地代表氢、氟、氯、-CF3、氰基或C1-6烷基，使得R1、R2、R3、R4和R5中至少有一个不是氢；R6、R7、R8、R9、R10和R11各自独立地代表氢或C1-6烷基；X代表连接子，选自键、-(CH2)n-和-O-(CH2)n-；n代表1至3的整数。这些化合物或盐能够调节P2X7受体功能，并能拮抗ATP在P2X7受体上的效应（“P2X7受体拮抗剂”）。
• A palladium-catalyzed dehydrative <i>N</i>-benzylation/C–H benzylation cascade of 2-morpholinoanilines on water
  作者：Hidemasa Hikawa、Risa Ichinose、Shoko Kikkawa、Isao Azumaya

  DOI：10.1039/c7gc03780e

  日期：——

  A strategy for the palladium-catalyzed dehydrative tandem benzylation of 2-morpholinoanilines with benzyl alcohols has been developed. This cascade reaction is devised as a straightforward and efficient synthetic route for N-(1,2-diphenylethyl)-2-morpholinoanilines in moderate to good yields (50–81%). The dehydrative sp3 C–H bond benzylation proceeds chemoselectively at the benzylic position of N-

  已经开发了用苯甲醇钯催化2-吗啉代苯胺的脱水串联苄基化的策略。该级联反应被设计为N-（1,2-二苯乙基）-2-吗啉代苯胺的简单有效的合成途径，产率中等至良好（50-81％）。脱水的sp 3 C–H键苄基化反应在N-苄基-2-吗啉代苯胺的苄基位置发生化学选择性，形成一个新的C（sp 3）–C（sp 3）键。KIE实验表明，CH键的活化参与了速率确定步骤（KIE = 2.7）。Hammett对2-吗啉代苯胺的研究得出负ρ值，表明在过渡态中存在正电荷的积累。可以在温和的反应条件下实现“水上”方案，该方案以水作为唯一的副产物提供相应的所需产品，而无需在原子经济过程中使用碱或其他添加剂。
• Ortho-substituted phenyl amidine and phenyl guanidine derivatives and antidiabetic or hypoglycaemic agents containing them
  申请人：The Boots Company PLC

  公开号：EP0385038A1

  公开（公告）日：1990-09-05

  Compounds of formula I and their salts in which n = 0 or 1, R1 and R2 are each aliphatic or cycloalkyl or NR1 R2 is an optionally substituted heterocyclic ring, R3 is alkyl, cycloalkyl or optionally substituted amino, R5 is an aliphatic group, R6 is H, an optionally substituted aliphatic group or a cycloalkyl group, or R3 and R5 together with the nitrogen and carbon atoms to which they are attached form an optionally substituted heterocyclic ring or R5 and R6 together with the nitrogen to which they are attached form a heterocyclic ring optionally substituted by alkyl and R7 is optionally substituted alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkoxycarbonyl, trifluoromethyl or cyano have utility as hypoglycaemic agents.

  式 I 的化合物及其盐类 及其盐类，其中 n = 0 或 1，R1 和 R2 各为脂肪族或环烷基或 NR1 R2 为任选取代的杂环，R3 为烷基、环烷基或任选取代的氨基，R5 为脂肪族基团，R6 为 H、任选取代的脂肪族基团或环烷基基团、或 R3 和 R5 与它们所连接的氮原子和碳原子一起形成一个任选取代的杂环，或 R5 和 R6 与它们所连接的氮原子一起形成一个任选被烷基取代的杂环，R7 是任选取代的烷基、烷氧基、烷硫基、烷基亚砜基、烷基磺酰基、烷氧基羰基、三氟甲基或氰基。
• Discovery of Potent, Selective Stem Cell Factor Receptor/Platelet Derived Growth Factor Receptor Alpha (c-KIT/PDGFRα) Dual Inhibitor for the Treatment of Imatinib-Resistant Gastrointestinal Stromal Tumors (GISTs)
  作者：Yanli Lu、Fei Mao、Xiaokang Li、Xinyu Zheng、Manjiong Wang、Qing Xu、Jin Zhu、Jian Li

  DOI：10.1021/acs.jmedchem.7b00468

  日期：2017.6.22

  Stem cell factor receptor (c-KIT) and platelet derived growth factor receptor alpha (PDGFR alpha) kinasts play an important role in gastrointestinal stromal tumors (GISTs). Here, we have discovered an c-KIT/PDGFR alpha dual inhibitor, compound 31, with single-digit nanomolar potency against c-KIT and PDGFRa. Compared to Imatinib (1), 31 showed better antiproliferative efficacy against various TEL-c-KIT/PD GFR alpha-BaF3 isogenic cells, including three 1-resistant BaF3 cell lines, as well as against GIST-T1 and GIST-882 cell lines. Furthermore, compound 31 showed a good KinomeScan selectivity (468 kinases) (S score (1) = 0.01 at 1 mu M concentration), good metabolic stability in liver microsomes, and no hERG inhibitory activity. It was worth noting that 31 inhibited GIST-T1 tumor growth (TGI = 81.5%) and even the BaF3-TEL-cKIT-T6701 tumor progression (TGI = 41.9%, 1-resistant GISTs) at a dosage of 100 mg/kg/day without exhibiting apparent toxicity.
• US4123251A
  申请人：——

  公开号：US4123251A

  公开（公告）日：1978-10-31