1-(2-amino-4,5-dimethoxyphenyl)propan-1-one | 4765-46-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(2-amino-4,5-dimethoxyphenyl)propan-1-one
• CAS: 4765-46-2
• 化学式: C₁₁H₁₅NO₃
• 分子量: 209.245
• InChiKey: OSZLLSFVPZYETG-UHFFFAOYSA-N

物化性质

• 熔点：
  128–129°C

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  61.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(2-amino-4,5-dimethoxyphenyl)propan-1-one 在 吡啶 、 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 0.33h， 生成 2-(1-hydroxypropyl)-4,5-dimethoxy-1-(4-methylphenylsulfonamido)benzene
  参考文献：
  名称：

  Simple route to 3-(2-indolyl)-1-propanones via a furan recyclization reaction

  摘要：

  A simple route to 1-R-3-(2-indolyl)-1-propanones has been elaborated based on recyclization of 2-(2-aminobenzyl)furan derivatives. Being a modification of the Reissert indole synthesis, our approach employs the furan ring as a source of carbonyl function. This approach is general and allows varying of substituents in aromatic ring as well as in 3-position of indole nucleus. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.10.056
• 作为产物：
  描述：

  1-(4,5-dimethoxy-2-nitrophenyl)-1-propanone 在 铁粉 、 溶剂黄146 作用下， 以 水 、 乙酸乙酯 为溶剂， 反应 6.0h， 以68%的产率得到1-(2-amino-4,5-dimethoxyphenyl)propan-1-one
  参考文献：
  名称：

  Simple route to 3-(2-indolyl)-1-propanones via a furan recyclization reaction

  摘要：

  A simple route to 1-R-3-(2-indolyl)-1-propanones has been elaborated based on recyclization of 2-(2-aminobenzyl)furan derivatives. Being a modification of the Reissert indole synthesis, our approach employs the furan ring as a source of carbonyl function. This approach is general and allows varying of substituents in aromatic ring as well as in 3-position of indole nucleus. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.10.056

文献信息

• Synthesis of 4-Alkylidene-4<i>H</i>-3,1-benzoxazine Derivatives by Acid-Catalyzed Cyclization of 2-Isocyanophenyl Ketones in the Presence of a Vinyl Ether
  作者：Kazuhiro Kobayashi、Yuta Okamura、Hisatoshi Konishi

  DOI：10.1055/s-0028-1087997

  日期：——

  2-(1-Alkoxyalkyl)-4-alkylidene-4H-3,1-benzoxazines are conveniently prepared by the reaction of 1-(2-isocyanophenyl)ethanones or 1-(2-isocyanophenyl)propan-1-ones with a vinyl ether, such as 2-methoxypropene or ethyl vinyl ether, in the presence of a catalytic amount of (±)-camphor-10-sulfonic acid. 4H-3,1-benzoxazines - acid-catalyzed reaction - fused-ring system - isocyanides - vinyl ethers

  2-（1-烷氧基烷基）-4-亚烷基-4 H -3,1-苯并恶嗪可通过1-（2-异氰基苯基）乙炔或1-（2-异氰基苯基）丙-1-酮与环己烯的反应方便地制备。乙烯基量，例如2-甲氧基丙烯或乙基乙烯基醚，在催化量的（±）-樟脑-10-磺酸的存在下。 4 H -3,1-苯并恶嗪-酸催化反应-稠环系统-异氰酸酯-乙烯基醚
• Synthesis and Antitumor Activity of 20(S)-Camptothecin Derivatives. A-Ring-Substituted 7-Ethylcamptothecins and Their E-Rig-Modified Water-Soluble Derivatives.
  作者：Takashi YAEGASHI、Seigo SAWADA、Hiroshi NAGATA、Tomio FURUTA、Teruo YOKOKURA、Tadashi MIYASAKA

  DOI：10.1248/cpb.42.2518

  日期：——

  Twenty-six novel A-ring-modified 7-ethylcamptothecins (6) were synthesized by Friedlander's condensation of the chiral tricyclic ketone (5) with aminopropiophenones (4). The compounds substituted with fluorine at the 11 position showed strong cytotoxicity to KB and L1210 cells. The 11-fluoro derivatives also exhibited strong inhibitory activity on DNA topoisomerase I. Nine compounds 6 with four to ten times stronger cytotoxicity than that of camptothecin were selected and converted into water-soluble 17-O-acyl amide derivatives (8). Compounds 8e (10-Me, O-COCH2CH2SCH3) and 8f (11-F, O-COC2H5) showed activity towards Meth A in mice that was comparable to that of CPT-11, at lower doses than CPT-11.

  合成了二十六种新型A环修饰的7-乙基喜树碱（6），通过Friedlander缩合反应，将手性三环酮（5）与氨基丙酮芳香化合物（4）进行反应。11位取代氟的化合物对KB细胞和L1210细胞表现出强烈的细胞毒性。11-氟衍生物在DNA拓扑酶I上的抑制活性也很强。选择了九种细胞毒性比喜树碱强四到十倍的化合物6，并将其转化为水溶性的17-O-酰胺衍生物（8）。化合物8e（10-甲基，O-COCH2CH2SCH3）和8f（11-氟，O-COC2H5）在小鼠中对Meth A的活性与CPT-11相当，且所需剂量低于CPT-11。
• Camptothecin derivatives
  申请人：Kabushiki Kaisha Yakult Honsha

  公开号：US05061800A1

  公开（公告）日：1991-10-29

  New campotothecin derivatives and a process for preparing same are disclosed, which are represented by the general formula: ##STR1## wherein R.sup.1 represents a lower alkyl group, R.sup.2 represents a hydrogen atom or an amino, hydroxyl, lower acylamino or lower alkoxy group, R.sup.3 represents a hydrogen or halogen atom or a lower alkyl, hydroxyl, lower alkoxy, nitro, amino, cyano or di(lower alkyl)amino group, R.sup.4 represents a hydrogen or halogen atom or a lower alkyl, hydroxyl, lower alkoxy, lower alkylthio, amino, cyano or di(lower alkyl)amino group, and R.sup.5 represents a hydrogen or halogen atom or a hydroxyl or lower alkoxy group, with the proviso that all of the R.sup.2, R.sup.3, R.sup.4 and R.sup.5 substituents should not be a hydrogen atom and also that if any one of the R.sup.2, R.sup.3, R.sup.4 and R.sup.5 is a hydroxyl or lower alkoxy group, all of the other three substituents should not be a hydrogen atom.

  揭示了新的紫杉醇衍生物及其制备方法，其通式表示为：其中R.sup.1代表低碳基团，R.sup.2代表氢原子或氨基、羟基、低酰胺基或低烷氧基，R.sup.3代表氢原子或卤素原子或低碳基、羟基、低烷氧基、硝基、氨基、氰基或二(低碳基)氨基，R.sup.4代表氢原子或卤素原子或低碳基、羟基、低烷氧基、低烷硫基、氨基、氰基或二(低碳基)氨基，R.sup.5代表氢原子或卤素原子或羟基或低烷氧基，但要注意所有的R.sup.2、R.sup.3、R.sup.4和R.sup.5取代基不应为氢原子，且如果R.sup.2、R.sup.3、R.sup.4和R.sup.5中的任何一个是羟基或低烷氧基，其他三个取代基都不应为氢原子。
• Copper-catalyzed oxidative amination of methanol to access quinazolines
  作者：Gandhesiri Satish、Ashok Polu、Laxman Kota、Andivelu Ilangovan

  DOI：10.1039/c9ob00392d

  日期：——

  copper-catalyzed oxidative amination of 2′-aminoarylketones with methanol as a C1 carbon source and ammonium acetate as an amine source to construct quinazolines was established in a one-pot manner. The reaction conditions are straightforward and highly atom economic to deliver the corresponding quinazolines in high yields with wide functional group tolerance. Importantly, the present method is applicable on a multigram

  以一锅法建立了一种以甲醇为碳碳源，乙酸铵为胺源的2'-氨基芳酮铜催化氧化胺化制备喹唑啉的新方法。该反应条件简单明了且原子经济性强，能够以高收率和宽泛的官能团耐受性提供相应的喹唑啉。重要的是，本方法可用于数克规模，并且其合成实用性通过高产率地合成肌肉松弛药物夸唑定而得到证明。
• [EN] IMINO SULFANONE INHIBITORS OF ENPP1<br/>[FR] INHIBITEURS IMINO SULFANONE DE L'ENPP1
  申请人：VOLASTRA THERAPEUTICS INC

  公开号：WO2021225969A1

  公开（公告）日：2021-11-11

  The present disclosure relates generally to inhibitors of ectonucleotide pyrophosphatase/phosphodiesterase 1 (ENPP1), compositions thereof, and methods of using said compounds and compositions thereof. More specifically, the present disclosure relates to sulfoximine- based inhibitors of ENPP1 of Formula (I) and methods of their use for treating disease mediated by ENPP1.

  本公开涉及一般来说是对细胞外核苷酸焦磷酸酶/磷酸二酯酶1（ENPP1）的抑制剂，其组合物以及使用所述化合物和组合物的方法。更具体地说，本公开涉及基于砜亚胺的ENPP1抑制剂，其化学式为（I），以及其用于治疗由ENPP1介导的疾病的方法。