3,4-ethylenedioxy-5-methoxybenzoic acid methyl ester | 287717-13-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3,4-ethylenedioxy-5-methoxybenzoic acid methyl ester
• 英文别名: methyl 8-methoxy-2,3-dihydrobenzo[b][1,4]dioxine-6-carboxylate；methyl 8-methoxy-2,3-dihydro-1,4-benzodioxin-6-carboxylate；methyl 3-methoxy-4,5-ethylenedioxybenzoate；methyl 5-methoxy-2,3-dihydro-1,4-benzodioxine-7-carboxylate
• CAS: 287717-13-9
• 化学式: C₁₁H₁₂O₅
• 分子量: 224.213
• InChiKey: ZJZGJCCWVJTNBK-UHFFFAOYSA-N

物化性质

• 沸点：
  293.1±7.0 °C(Predicted)
• 密度：
  1.243±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3,4-ethylenedioxy-5-methoxybenzoic acid methyl ester 在 一水合肼 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 121.0h， 生成 N-butyl-2-(8-methoxy-2,3-dihydrobenzo[b][1,4]dioxine-6-carbonyl)hydrazine-1-carbothioamide
  参考文献：
  名称：

  Design, synthesis and anticancer evaluation of novel 1,3-benzodioxoles and 1,4-benzodioxines

  摘要：

  A new set of 1,3-benzodioxoles and 1,4-benzodioxines was designed and synthesized starting from gallic acid as anticancer agents. The antiproliferative effect of the target compounds was evaluated against a panel of cancer cell lines (HepG2, PC-3, MCF-7 and A549) using MTT assay. The 1,4-benzodioxine derivative 11a manifested broad spectrum effect towards the four tested cancer cell lines (IC₅₀ < 10 μM) with lower toxic effect on normal human cell line BJ1. Cell cycle progression of MCF-7 after treatment with compound 11a was studied where it induced cells accumulation at G2/M phase as well as increasing in the percentage of cells at pre-G1. Compound 11a is found to be a tubulin polymerization inhibitor with IC₅₀ = 6.37 μM. Also, flow cytometeric analysis revealed that compound 11a could induce both early and late stage apoptosis in MCF-7 cell line. Moreover, the ability of this compound to stimulate apoptosis in the latter cell line was further confirmed by: increment of Bax/Bcl-2 ratio, increase the expression of tumor suppressor gene p53, boosting the levels of initiator and executioner caspases as well as raise in the amount of cytochrome C. In addition molecular docking study was accomplished on the colchicine binding site of tubulin (pdb: 1SA0) to illustrate the interactions of the most potent compound 11a to the receptor.

  DOI：

  10.1016/j.ejps.2019.105045
• 作为产物：
  描述：

  没食子酸甲酯 在 Sodium tetraborate decahydrate 、 potassium carbonate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 28.17h， 生成 3,4-ethylenedioxy-5-methoxybenzoic acid methyl ester
  参考文献：
  名称：

  设计和合成新型抗仲巴拉圭酸衍生物作为抗惊厥药。

  摘要：

  在这项工作中，合成了一组新的对羟基苯甲酸9a-d，12a-d和13a-d的衍生物，并评估了它们的抗惊厥潜能。所有被研究的化合物在scPTZ和MES测试中均显示出抗惊厥活性。在II期抗惊厥研究中，在scPTZ测试中，三甲氧基苯基衍生物9a在被测化合物中具有最高的效力。它显示出比标准药物苯巴比妥和乙巯乙酰亚胺分别高1.72倍和17.05倍的活性。此外，化合物9a的安全性范围比参考抗癫痫药ethosuximide的安全性更好。同样，化合物9a没有肝毒性，这是通过测量血清ALT，AST，ALP，白蛋白和总蛋白来表明的。此外，化合物9a的治疗可将GABA脑水平显着提高2。与对照值相比，高56倍。此外，在GABA-AT的活性位点上进行了分子对接，以阐明最有效的化合物9a与酶的相互作用。在MES测试中，化合物12a对电刺激诱发的癫痫发作表现出最强的活性，最低的ED50 = 13.7 mg / kg，保护指数>

  DOI：

  10.1016/j.bioorg.2019.103473

文献信息

• Substituted 4-(1H-benzimidazol-2-yl-amino)piperidines useful for the treatment of allergic diseases
  申请人：Aventis Pharmaceuticals Inc.

  公开号：US06211199B1

  公开（公告）日：2001-04-03

  The present invention relates to novel substituted piperidine derivatives of formula (1), stereoisomers thereof, and pharmaceutically acceptable salts thereof which are useful as histamine receptor antagonists and tachykinin receptor antagonist. Such antagonists are useful in the treatment of allergic rhinitis, including seasonal rhinitis and sinusitis; inflammatory bowel diseases, including Crohn's disease and ulcerative colitis; asthma; bronchitis; and emesis.

  本发明涉及一种新型的取代哌啶衍生物，其化学式为（1），其立体异构体以及药学上可接受的盐，这些衍生物可用作组胺受体拮抗剂和速激肽受体拮抗剂。这些拮抗剂在过敏性鼻炎的治疗中很有用，包括季节性鼻炎和鼻窦炎；炎症性肠病，包括克罗恩病和溃疡性结肠炎；哮喘；支气管炎；以及呕吐。
• Novel substituted 4-(1H-benzimidazol-2-yl) [1,4]diazepanes useful for the treatment of allergic diseases
  申请人：——

  公开号：US20010034343A1

  公开（公告）日：2001-10-25

  The present invention relates to novel 4-(1H-benzimidazol-2-yl)[1,4]diazepane derivatives of formula 1 and stereoisomers thereof, and pharmaceutically acceptable salts thereof which are useful as histamine receptor antagonists and tachykinin receptor antagonist. Such antagonists are useful in the treatment of allergic rhinitis, including seasonal rhinitis and sinusitis; inflammatory bowel diseases, including Crohn's disease and ulcerative colitis; asthma; bronchitis; and emesis.

  本发明涉及一种新颖的4-(1H-苯并咪唑-2-基)[1,4]二氮杂环庚烷衍生物及其立体异构体，以及其药学上可接受的盐，其作为组胺受体拮抗剂和速激肽受体拮抗剂具有用途。这些拮抗剂在过敏性鼻炎的治疗中有用，包括季节性鼻炎和鼻窦炎；炎症性肠病，包括克罗恩病和溃疡性结肠炎；哮喘；支气管炎；以及呕吐。
• Substituted 4-(1H-benzimidazol-2-yl)&lsqb;1,4&rsqb;diazepanes useful for the treatment of allergic disease
  申请人：Aventis Pharmaceuticals Inc.

  公开号：US06194406B1

  公开（公告）日：2001-02-27

  The present invention relates to novel 4-(1H-benzimidazol-2-yl)[1,4]diazepane derivatives of formula (1): and stereoisomers thereof, and pharmaceutically acceptable salts thereof which are useful as histamine receptor antagonists and tachykinin receptor antagonist. Such antagonists are useful in the treatment of allergic rhinitis, including seasonal rhinitis and sinusitis; inflammatory bowel diseases, including Crohn's disease and ulcerative colitis; asthma; bronchitis; and emesis.

  本发明涉及新颖的4-(1H-苯并咪唑-2-基)[1,4]二氮杂环庚烷衍生物的化合物（1）及其立体异构体，以及其药学上可接受的盐，这些化合物可用作组胺受体拮抗剂和速激肽受体拮抗剂。这些拮抗剂在过敏性鼻炎的治疗中很有用，包括季节性鼻炎和鼻窦炎；炎症性肠病，包括克罗恩病和溃疡性结肠炎；哮喘；支气管炎；以及呕吐。
• NOVEL NITROGENATED HETEROCYCLIC COMPOUND AND SALT THEREOF
  申请人：Kiyoto Taro

  公开号：US20100168418A1

  公开（公告）日：2010-07-01

  A nitrogen-containing heterocyclic compound represented by the general formula: wherein the dashed line represents a single bond or a double bond; R 1 , R 2 , R 3 , R 4 and R 5 independently represent a hydrogen atom, halogen atom, a lower alkyl, aryl, lower alkoxy or monocyclic heterocyclic group which may be substituted or the like; R 6 represents a lower alkyl, aryl, monocyclic heterocyclic, bicyclic heterocyclic or tricyclic heterocyclic group which may be substituted; X 1 represents a lower alkylene group or the like; X 2 represents a lower alkylene, lower alkenylene or lower alkynylene group which may be substituted; X 3 represents an oxygen atom, sulfur atom, a sulfinyl group, sulfonyl group or the like; Y 1 represents a bivalent cyclic group, containing a nitrogen, which may be substituted or the like; and Z 1 represents a nitrogen atom, a carbon atom which may be substituted or the like, or a salt thereof. The compound or salt has a potent antibacterial activity and a high safety, and is therefore useful as an excellent antibacterial agent.

  一种含氮杂环化合物，通式如下：其中虚线代表单键或双键；R1、R2、R3、R4和R5分别独立地代表氢原子、卤素原子、较低的烷基、芳基、较低的烷氧基或可以被取代的单环杂环基等；R6代表较低的烷基、芳基、单环杂环、双环杂环或三环杂环基，可以被取代；X1代表较低的烷基亚基或类似物；X2代表可以被取代的较低烷基、较低烯基或较低炔基亚基；X3代表氧原子、硫原子、亚砜基、磺酰基或类似物；Y1代表含有氮的二价环状基团，可以被取代或类似物；Z1代表氮原子、可以被取代的碳原子或类似物，或其盐。该化合物或盐具有强效的抗菌活性和高度的安全性，因此可用作优良的抗菌剂。
• QUINOLINONES AND QUINOXALINONES AS ANTIBACTERIAL COMPOSITION
  申请人：KIYOTO Taro

  公开号：US20120214990A1

  公开（公告）日：2012-08-23

  A nitrogen-containing heterocyclic compound or pharmaceutically acceptable salt thereof represented by the general formula: which have a potent antibacterial activity and a high safety. Thus, the compounds are useful as antibacterial agents against gram-positive bacteria, gram-negative bacteria and drug resistant bacteria.

  一种含氮杂环化合物，或其药学上可接受的盐，其通式如下：具有强效的抗菌活性和高安全性。因此，这些化合物可用作抗革兰阳性菌、抗革兰阴性菌和抗药性菌的抗菌剂。