3-甲氧基-2-氨基苯甲酰胺 | 106782-78-9

• 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: 3-甲氧基-2-氨基苯甲酰胺
• 英文名称: 2-amino-3-methoxybenzamide
• 英文别名: 3-methoxy-2-aminobenzamide
• CAS: 106782-78-9
• 化学式: C₈H₁₀N₂O₂
• 分子量: 166.18
• InChiKey: KTSGITANKLIJRS-UHFFFAOYSA-N

物化性质

• 熔点：
  162-164°C
• 沸点：
  280.7±25.0 °C(Predicted)
• 密度：
  1.236±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于二甲基亚砜、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  78.3
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2924299090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  存储条件：2-8°C，密封保存，干燥环境并避免光照。

反应信息

• 作为反应物：
  描述：

  3-甲氧基-2-氨基苯甲酰胺 在 吡啶 、 三溴化硼 、 potassium carbonate 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 34.0h， 生成 8-羟基-2,3-二甲基-4(3H)-喹唑啉酮
  参考文献：
  名称：

  Resistance-Modifying Agents. 5. Synthesis and Biological Properties of Quinazolinone Inhibitors of the DNA Repair Enzyme Poly(ADP-ribose) Polymerase (PARP)

  摘要：

  Clinical studies concerning the role of poly(ADP-ribose) polymerase (PARP) in the repair of drug- and radiation-induced DNA damage have been impeded by the poor solubility, lack of potency, and limited specificity of currently available inhibitors. A series of 2-alkyl- and 2-aryl-substituted 8-hydroxy-, 8-methoxy-, and 8-methylquinazolin-4(3H)-ones has been synthesized and evaluated for PARP inhibitory activity in permeabilized L1210 murine leukemia cells. 8-Methoxy- and 8-methylquinazolinones (14-34) were readily prepared by acylation of 3-substituted anthranilamides with the appropriate acid chloride, followed by base-catalyzed cyclization. The requisite 8-hydroxyquinazolinones (6, 35-39) were synthesized by demethylation of the corresponding 8-methoxyquinazolinones with BBr3. N-Methylation of 8-methoxy-2-methylquinazolinone (15) with Mel, followed by O-demethylation by BBr3, afforded the control N-3-methylquinazolinones 42 and 43, respectively. In general, an 8-hydroxy or 8-methyl substituent enhanced inhibitory activity in comparison with an 8-methoxy group. 2-Phenylquinazolinones were marginally less potent than the corresponding 2-methylquinazolinones, but the introduction of an electron-withdrawing or electron-donating 4'-substituent on the 2-aryl ring invariably increased potency. This was particularly evident in the 8-methylquinazolinone series (IC50 values 0.13-0.27 mu M), which are among the most potent PARP inhibitors reported to date. N-3-Methylquinazolinones 42 and 43 were essentially devoid of activity (IC50 values > 100 mu M). In studies with L1210 cells in vitro, a concentration of 200 mu M 8-hydroxy-2-methylquinazolinone (6, NU1025) (IC50 value 0.40 mu M) potentiated the cytotoxicity of the monomethylating agent 5-(3-methyltriazen-1-yl)imidazole-4-carboxamide and gamma-radiation 3.5- and 1.4-fold, respectively, at the 10% survival level.

  DOI：

  10.1021/jm980273t
• 作为产物：
  描述：

  2-氨基-3-甲氧基苯甲酸 在 碳酸氢铵 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 24.5h， 生成 3-甲氧基-2-氨基苯甲酰胺
  参考文献：
  名称：

  镍催化含芳基腈的 1,2,3-苯并三嗪-4(3H)-酮的分子内双环化反应：合成洛托宁 A 及相关多环吡咯并喹唑啉酮的途径

  摘要：

  在此，我们报道了含芳基腈的1,2,3-苯并三嗪-4(3 H )-酮的镍催化分子内脱氮双环化反应，合成了具有多种取代基的多环吡咯并喹唑啉酮。该催化反应是1,2,3-苯并三嗪-4(3H)-酮与腈的首次脱氮转环反应，可作为合成洛托宁A的关键步骤，具有较高的步骤经济性。

  DOI：

  10.1021/acs.orglett.3c03142

文献信息

• Condensation of anthranilic acids with pyridines to furnish pyridoquinazolones via pyridine dearomatization
  作者：Yajun Yang、Cuiju Zhu、Min Zhang、Shijun Huang、Jingjing Lin、Xiandao Pan、Weiping Su

  DOI：10.1039/c6cc07365d

  日期：——

  The unprecedented carbodiimide-mediated condensation between pyridines and anthranilic acids via pyridines dearomatization at room temperature has been developed to provide a straightforward approach to pyridoquinazolones. The value of this approach...

  已经开发出前所未有的碳二亚胺介导的吡啶与邻氨基苯甲酸之间在室温下经由吡啶脱芳香化作用的缩合反应，从而为吡啶基喹唑酮提供了直接的方法。这种方法的价值...
• Preparation of thiazolo (2,3-b) zuinazolones
  申请人：BASF Aktiengesellschaft

  公开号：US05030727A1

  公开（公告）日：1991-07-09

  The process of manufacturing thiazolo-(2,3-b)-quinoazolones of the formula I ##STR1## where R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are defined in the disclosure, wherein either a) an anthranilamide derivative of the formula II ##STR2## where R.sup.5 and R.sup.6 are hydrogen or C.sub.1 -C.sub.4 -alkyl, is reacted with a thiazole derivative of the formula III ##STR3## where X is fluorine, chlorine, bormine, alkylsulfonyl or arylsulfonyl, or b) for certain radicals R.sup.4' from the group R.sup.4 - a thiazolo-(2,3-b)-quinazolone of the general formula IV ##STR4## is reacted with a nucleophile R.sup.4' -H, where R.sup.4' is alkoxy, alkylthio or unsubstituted or halogen-, alkyl-, haloalkyl-, nitro- or alkoxy-substituted phenoxy or thiophenyl, or an alkali metal, alkaline earth metal or ammonium salt of an alcohol.

  制造式I的噻唑并[2,3-b]喹唑酮的过程如下：其中R.sup.1、R.sup.2、R.sup.3和R.sup.4在披露中有定义，其中a)式II的蒽酰胺衍生物与式III的噻唑衍生物发生反应，其中R.sup.5和R.sup.6为氢或C.sub.1-C.sub.4-烷基，其中X为氟、氯、溴、烷基磺酰基或芳基磺酰基；或b)对于来自R.sup.4组的某些基团R.sup.4'，通式IV的噻唑并[2,3-b]喹唑酮与亲核试剂R.sup.4'-H发生反应，其中R.sup.4'为烷氧基、烷基硫醚基或未取代或卤代、烷基、卤代烷基、硝基或烷氧基取代的苯氧基或硫代苯基，或醇的碱金属、碱土金属或铵盐。
• Efficient Route to Deuterated Aromatics by the Deamination of Anilines
  作者：Kristyna Burglova、Sergei Okorochenkov、Jan Hlavac

  DOI：10.1021/acs.orglett.6b01438

  日期：2016.7.15

  One-step replacement of NH2 groups in ring-substituted anilines by deuterium is reported. Approaches comprising both solid-phase and solution-phase syntheses can be used on a large variety of substrates. The method uses diazotization in a mixture of water and either dichloromethane or chloroform, which serve as a source of hydrogen. This protocol can be used as a general method for fast and easy incorporation

  据报道，氘能一步取代环取代苯胺中的NH 2基团。包括固相合成和溶液相合成的方法都可以用于多种基质上。该方法在水和二氯甲烷或氯仿的混合物中使用重氮化作用，而二氯甲烷或氯仿是氢的来源。该方案可以用作使用氘化氯仿将氘快速轻松地掺入芳族体系的一般方法。
• SUBSTITUTED 2- AMIDOQUINAZOL-4-ONES AS MATRIX METALLOPROTEINASE-13 INHIBITORS
  申请人：Takeda Pharmaceutical Company Limited

  公开号：US20150329556A1

  公开（公告）日：2015-11-19

  The present invention provides a novel amide derivative having a matrix metalloproteinase inhibitory activity, and useful as a pharmaceutical agent, which is a compound represented by the formula (I) wherein ring A is an optionally substituted, nitrogen containing heterocycle, ring B is an optionally substituted monocyclic homocycle or an optionally substituted monocyclic heterocycle, Z is N or NR 1 (R 1 is a hydrogen atom or an optionally substituted hydrocarbon group), is a single bond or a double bond, R 2 is a hydrogen atom or an optionally substituted hydrocarbon group, X is an optionally substituted spacer having 1 to 6 atoms, ring C is (1) an optionally substituted homocycle or (2) an optionally substituted heterocycle other than a ring represented by (II) (X′ is S, O, SO, or CH 2 ), and at least one of ring B and ring C has substituent(s), provided that N-(1S,2R)-1-(3,5-difluorobenzyl)-3-[(3-ethylbenzyl)amino]2 hydroxypropyl}5,6 dimethyl 4 oxo 1,4 dihydrothieno[2,3-d]pyrimidine-2-carboxamide is excluded, or a salt thereof.

  本发明提供了一种新型酰胺衍生物，具有基质金属蛋白酶抑制活性，并且作为药用剂是有用的，该化合物由以下式(I)表示，其中环A是一个可选择取代的含氮杂环，环B是一个可选择取代的单环同核环或可选择取代的单环杂环，Z是N或NR1（R1是氢原子或可选择取代的碳氢基团），是一个单键或双键，R2是氢原子或可选择取代的碳氢基团，X是一个具有1到6个原子的可选择取代的间隔物，环C是（1）一个可选择取代的同核环或（2）一个除了由（II）表示的环之外的可选择取代的杂环（X′是S、O、SO或CH2），并且环B和环C中至少有一个有取代基，但不包括N-(1S,2R)-1-(3,5-二氟苄基)-3-[(3-乙基苄基)氨基]2-羟基丙基}5,6-二甲基-4-氧代-1,4-二氢噻唑并[2,3-d]嘧啶-2-羧酰胺，或其盐。
• Anti-inflammatory agents
  申请人：Hansen Henrik C.

  公开号：US09238640B2

  公开（公告）日：2016-01-19

  Disclosed are novel compounds that are useful in regulating the expression of interleukin-6 (IL-6) and/or vascular cell adhesion molecule-1 (VCAM-1), and their use in the treatment and/or prevention of cardiovascular and inflammatory diseases and related disease states, such as, for example, atherosclerosis, asthma, arthritis, cancer, multiple sclerosis, psoriasis, and inflammatory bowel diseases, and autoimmune disease(s). Also, disclosed are compositions comprising the novel compounds, as well as methods for their preparation.

  揭示了一种新型化合物，可用于调节白细胞介素-6（IL-6）和/或血管细胞粘附分子-1（VCAM-1）的表达，并且它们在治疗和/或预防心血管和炎症性疾病以及相关疾病状态中的用途，例如动脉粥样硬化、哮喘、关节炎、癌症、多发性硬化、牛皮癣和炎症性肠病以及自身免疫疾病。此外，还揭示了包含这些新型化合物的组合物，以及它们的制备方法。