2-氨基-n,5-二甲氧基-n-甲基苯甲酰胺 | 214971-09-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-氨基-n,5-二甲氧基-n-甲基苯甲酰胺
• 英文名称: 2-amino-5,N-dimethoxy-N-methylbenzamide
• 英文别名: 2-amino-N,5-dimethoxy-N-methylbenzamide；N-methyl-N-methyloxy 2-amino-5-methyloxy-benzamide；2-amino-N-methyl-N,5-bis(methyloxy)benzamide；Benzamide, 2-amino-N,5-dimethoxy-N-methyl-
• CAS: 214971-09-2
• 化学式: C₁₀H₁₄N₂O₃
• 分子量: 210.233
• InChiKey: CWLMVQZFAUWODA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  64.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-氨基-n,5-二甲氧基-n-甲基苯甲酰胺 在 正丁基锂 、 对甲苯磺酸 、 potassium iodide 、 sodium nitrite 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 反应 1.0h， 生成 2-iodo-5-methoxybenzophenone
  参考文献：
  名称：

  使用N-甲酰基糖精作为CO源的邻碘代-拴系亚甲基环丙烷（MCP）的钯催化级联还原和羰基化环化反应

  摘要：

  已开发了使用N-甲酰基糖精作为CO源的钯催化的邻-碘系链亚甲基环丙烷（MCP）的还原和羰基环化反应，以中等至良好的收率提供了所需的茚满酮衍生物，具有较高的区域和立体选择性以及良好的官能团相容性。

  DOI：

  10.1002/adsc.201901005
• 作为产物：
  描述：

  2-氨基-5-甲氧基苯甲酸 在 三乙胺 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 4.17h， 生成 2-氨基-n,5-二甲氧基-n-甲基苯甲酰胺
  参考文献：
  名称：

  Structure–Activity Relationships and Pharmacophore Model of a Noncompetitive Pyrazoline Containing Class of GluN2C/GluN2D Selective Antagonists

  摘要：

  Here we describe the synthesis and structure-activity relationship for a class of pyrazoline-containing dihydroquinolone negative allosteric modulators of the NMDA receptor that show strong subunit selectivity for GluN2C- and GluN2D-containing receptors over GluN2A- and GluN2B-containing receptors. Several members of this class inhibit NMDA receptor responses in the nanomolar range and are more than 50-fold selective over GluN1/GluN2A and GluN1/GluN2B NMDA receptors, as well as AMPA, kainate, GABA, glycine, nicotinic, serotonin, and purinergic receptors. Analysis of the purified enantiomers of one of the more potent and selective compounds shows that the S-enantiomer is both more potent and more selective than the R-enantiomer. The S-enantiomer had an IC50 of 0.17-0.22 mu M at GluN2D- and GluN2C-containing receptors, respectively, and showed over 70-fold selectivity over other NMDA receptor subunits. The subunit selectivity of this class of compounds should be useful in defining the role of GluN2C- and GluN2D-containing receptors in specific brain circuits in both physiological and pathophysiological conditions.

  DOI：

  10.1021/jm400652r

文献信息

• Lewis or Brønsted acid-catalysed reaction of propargylic alcohol-tethered alkylidenecyclopropanes with indoles and pyrroles for the preparation of polycyclic compounds tethered with indole or pyrrole motif
  作者：Hao-Zhao Wei、Liu-Zhu Yu、Min Shi

  DOI：10.1039/c9ob02211b

  日期：——

  derivatives via the Lewis or Brønsted acid catalysed cascade nucleophilic addition, electronic cyclization, ring-opening rearrangement of propargylic alcohol-tethered alkylidenecyclopropanes with indole and pyrrole derivatives. The reaction exhibited a broad substrate scope and good functional group tolerance under metal-free conditions, affording the desired products in moderate to good yields.

  我们开发了一种简便的合成方法，该方法可通过路易斯或布朗斯台德酸催化的级联亲核加成，电子环化，带有炔丙基和吡咯衍生物的炔丙醇系链亚烷基环丙烷的开环重排来访问环戊五烯[ b ]萘衍生物。该反应在无金属的条件下表现出宽泛的底物范围和良好的官能团耐受性，以中等至良好的产率提供了所需的产物。
• 4,1-benzoxazepines, their analogues, and their use as somatostatin agonists
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US06352982B1

  公开（公告）日：2002-03-05

  The present invention provides a compound of the formula: wherein ring A is an optionally substituted aromatic hydrocarbon ring or aromatic heterocyclic ring; ring B is an optionally substituted aromatic hydrocarbon ring or aromatic heterocyclic ring; Z is an optionally substituted cyclic group or linear hydrocarbon group; R1 is a hydrogen atom, an optionally substituted hydrocarbon group or heterocyclic ring; R2 is an optionally substituted amino group; D is a bond or an optionally substituted divalent hydrocarbon group; E is a bond, —CON(Ra)—, —N(Ra)CO—, —N(Rb)CON(Rc)—, —N(Rd)COO—, —N(Re)SO2—, —COO—, —N(Rf)—, —O—, —S— —SO—, —SO2—, (in which Ra, Rb, Rc, Rd, Re and Rf are respectively a hydrogen atom or an optionally substituted hydrocarbon group); G is a bond or an optionally divalent substituted hydrocarbon group; L is a divalent group; ring B may form an optionally substituted non-aromatic condensed nitrogen-containing heterocyclic ring by combining with R2; X is two hydrogen atoms, an oxygen atom or a sulfur atom; is a single bond or a double bond, and Y is a nitrogen atom when is a double bond, or an oxygen atom, —N(R4)— (in which R4 is a hydrogen atom, an optionally substituted hydrocarbon group or an acyl group) or S(O)n (in which n is 0, 1 or 2) when is a single bond, or a salt thereof, which have somatostatin receptor agonistic action.

  本发明提供了一种化合物，其化学式为： 其中环A是一个可选择取代的芳香烃环或芳香杂环；环B是一个可选择取代的芳香烃环或芳香杂环；Z是一个可选择取代的环状基团或线性碳氢基团；R1是一个氢原子，一个可选择取代的碳氢基团或杂环；R2是一个可选择取代的氨基团；D是一个键或一个可选择取代的二价碳氢基团；E是一个键，-CON(Ra)-，-N(Ra)CO-，-N(Rb)CON(Rc)-，-N(Rd)COO-，-N(Re)SO2-，-COO-，-N(Rf)-，-O-，-S-，-SO-，-SO2-， （其中Ra、Rb、Rc、Rd、Re和Rf分别是氢原子或一个可选择取代的碳氢基团）；G是一个键或一个可选择取代的二价碳氢基团；L是一个二价基团；环B可以通过与R2结合形成一个可选择取代的非芳香的含氮杂环；X是两个氢原子，一个氧原子或一个硫原子；是一个单键或一个双键，Y是一个氮原子，当是一个双键时，或一个氧原子，-N(R4)-（其中R4是一个氢原子，一个可选择取代的碳氢基团或酰基）或S(O)n（其中n为0、1或2）当是一个单键时，或其盐，具有生长抑素受体激动作用。
• [EN] COMPOUNDS WHICH INCREASE APOLIPOPROTEIN A-1 PRODUCTION AND USES THEREOF IN MEDICINE<br/>[FR] COMPOSES QUI AUGMENTENT LA PRODUCTION DE L'APOLIPOPROTEINE A-1 ET LEURS UTILISATIONS EN MEDECINE
  申请人：SMITHKLINE BEECHAM CORP

  公开号：WO2006032470A1

  公开（公告）日：2006-03-30

  The present invention relates to compounds of formula (I), pharmaceutically acceptable salts thereof, hydrates thereof, solvates thereof, prodrugs thereof and combinations thereof: wherein X represents CH or N; Y represents CH or N; R1 represents H or C1-2alkyl; R2 represents H or C1-4alkyl; R3 represents C1-6alkyl, carbocyclyl, carbocyclylC1-4alkyl, heterocyclyl or heterocyclylC1-4alkyl, wherein any of the carbocyclyl or heterocyclyl groups are optionally substituted by one or two groups selected from: halogen, C1-6alkyl, haloC1-6alkyl, hydroxyC1-6alkyl, C1-6alkoxy, haloC1-6alkoxy, nitro, cyano, -COH, -COOH, C1-6alkoxycarbonyl, C1-6alkylcarbonyl, -C(OH)R5R6 (wherein R5 and R6 independently represent H or C1-6alkyl), -(CH2)nNR3aR3b and -O(CH2)pNR3aR3b (wherein n represents 1, 2 or 3, p represents 2 or 3 and R3a and R3b independently represent H, C1-6alkyl or carbocyclylC1-4alkyl, or R3a and R3b together with the interconnecting atoms form a 5 or 6-membered ring which ring optionally contains one or two heteroatoms independently selected from the group consisting of O, S and N); R4 represents H, hydroxy, halo, C 1-6 alkyl, haloC1-6alkyl, hydroxyC1-6alkyl, C2-6alkenyl, C1-6alkoxy, haloC1-6alkoxy, carbocyclyl or heterocyclyl, wherein the carbocyclyl or heterocyclyl group is optionally substituted by one or two groups selected from: halogen, C1-6alkyl, haloC1-6alkyl, C1-6alkoxy, haloC1-6alkoxy, nitro and cyano; and provided that the compound is not: 7-chloro-5-phenyl-[1,2,4]triazolo[4,3-a]quinolin-4-amine; 7-chloro-1-methyl-5-phenyl[1,2,4]triazolo[4,3-a]quinolin-4-amine; or 7-chloro-5-(2-chlorophenyl)-1-methyl-1,2,4]triazolo[4,3-a]quinolin-4-amine. Also disclosed are pharmaceutical compositions containing the compounds and to their use in medicine. The compound exhibit increased apo-A1 production and are useful in the treatment for example a disease or condition caused by raised levels of LDL-cholesterol or by inflammation.

  本发明涉及以下式(I)的化合物，其在药学上可接受的盐、水合物、溶剂合物、前药及其组合物：其中X代表CH或N；Y代表CH或N；R1代表H或C1-2烷基；R2代表H或C1-4烷基；R3代表C1-6烷基、碳环烷基、碳环烷基C1-4烷基、杂环烷基或杂环烷基C1-4烷基，其中任何碳环烷基或杂环烷基基团可选择地由以下一种或两种基团取代：卤素、C1-6烷基、卤代C1-6烷基、羟基C1-6烷基、C1-6烷氧基、卤代C1-6烷氧基、硝基、氰基、-COH、-COOH、C1-6烷氧羰基、C1-6烷基羰基、-C(OH)R5R6（其中R5和R6独立地代表H或C1-6烷基）、-(CH2)nNR3aR3b和-O(CH2)pNR3aR3b（其中n代表1、2或3，p代表2或3，R3a和R3b独立地代表H、C1-6烷基或碳环烷基C1-4烷基，或R3a和R3b与相互连接的原子一起形成一个含有O、S和N中独立选择的一个或两个杂原子的5或6元环，R4代表H、羟基、卤素、C1-6烷基、卤代C1-6烷基、羟基C1-6烷基、C2-6烯基、C1-6烷氧基、卤代C1-6烷氧基、碳环烷基或杂环烷基，其中碳环烷基或杂环烷基基团可选择地由以下一种或两种基团取代：卤素、C1-6烷基、卤代C1-6烷基、C1-6烷氧基、卤代C1-6烷氧基、硝基和氰基；并且前提是该化合物不是：7-氯-5-苯基-[1,2,4]三唑并[4,3-a]喹啉-4-胺；7-氯-1-甲基-5-苯基[1,2,4]三唑并[4,3-a]喹啉-4-胺；或7-氯-5-(2-氯苯基)-1-甲基-[1,2,4]三唑并[4,3-a]喹啉-4-胺。还公开了含有这些化合物的药物组合物以及它们在医学上的用途。该化合物具有增加apo-A1产生并且在治疗例如由于LDL胆固醇水平升高或由于炎症引起的疾病或病症中是有用的。
• Synthesis of Diiodinated All-Carbon 3,3′-Diphenyl-1,1′-spirobiindene Derivatives via Cascade Enyne Cyclization and Electrophilic Aromatic Substitution
  作者：Quanzhe Li、Liuzhu Yu、Yin Wei、Min Shi

  DOI：10.1021/acs.joc.9b01418

  日期：2019.7.19

  from the reaction of propargyl alcohol-tethered alkylidenecyclopropanes with iodine. The reaction proceeded through an iodination-initiated cascade intramolecular enyne cyclization and electrophilic aromatic substitution reaction process in 1,2-dichloroethane upon heating, giving desired spirocyclic products in moderate to excellent yields. Further transformation of the obtained products has also been

  从炔丙醇系链的亚烷基亚环丙烷与碘的反应中，已经开发出一种用于合成二碘代全碳螺双联二烯衍生物的合成方法。该反应通过在1，2-二氯乙烷中加热时由碘化引发的级联分子内烯炔环化和亲电子芳族取代反应过程进行，以中等至优异的产率得到所需的螺环产物。还提出了所得产物的进一步转化。
• Asymmetric Synthesis of Hydroquinazolines Bearing C4-Tetrasubstituted Stereocenters via Kinetic Resolution of α-Tertiary Amines
  作者：Qianwen Jiang、Tianren Qin、Xiaoyu Yang

  DOI：10.1021/acs.orglett.1c04039

  日期：2022.1.21

  A novel protocol for asymmetric synthesis of hydroquinazolines bearing C4-tetrasubstituted stereocenters has been achieved through kinetic resolution of 2-amido α-tertiary benzylamines via chiral phosphoric acid catalyzed intramolecular dehydrative cyclizations. This method gave access to both α-tertiary benzylamines and hydroquinazolines with broad scope and high enantioselectivities. An intriguing

  通过手性磷酸催化的分子内脱水环化对 2-酰胺基 α-叔苄胺进行动力学拆分，实现了不对称合成带有 C4-四取代立体中心的氢喹唑啉的新方案。该方法获得了具有广泛范围和高对映选择性的 α-叔苄胺和氢喹唑啉。对于带有 C4-四取代立体中心的氢喹唑啉产物，观察到了有趣的 C-N 键旋转受限。