ethyl 5-amino-3-methylbenzofuran-2-carboxylate hydrochloride | 1333205-71-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: ethyl 5-amino-3-methylbenzofuran-2-carboxylate hydrochloride
• 英文别名: ethyl 5-amino-3-methyl-1-benzofuran-2-carboxylate hydrochloride；ethyl 5-amino-3-methyl-1-benzofuran-2-carboxylate;hydrochloride
• CAS: 1333205-71-2
• 化学式: C₁₂H₁₃NO₃*ClH
• 分子量: 255.701
• InChiKey: OBVUZGYAEMJSSZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.92
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  65.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 5-amino-3-methylbenzofuran-2-carboxylate hydrochloride 在 吡啶 、 potassium carbonate 、 potassium iodide 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 6.0h， 生成 ethyl 5-(N-benzyl-4-bromophenylsulfonamido)-3-methylbenzofuran-2-carboxylate
  参考文献：
  名称：

  Discovery and optimization of new benzofuran derivatives against p53-independent malignant cancer cells through inhibition of HIF-1 pathway

  摘要：

  p53-independent malignant cancer is still severe health problem of human beings. HIF-1 pathway is believed to play an important role in the survival and developing progress of such cancers. In the present study, with the aim to inhibit the proliferation of p53-independent malignant cells, we disclose the optimization of 6a, the starting compound which is discovered in the screening of in-house compound collection. The structure-activity relationship (SAR) is summarized. The most potent derivative 8d, inhibits the proliferation of both p53-null and p53-mutated cells through inhibition of HIF-1 pathway. Our findings here provide a new chemotype in designing potent anticancer agent especially against those p53-independent malignant tumors. (C) 2016 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2016.03.112
• 作为产物：
  描述：

  4'-甲氧基乙酰苯胺 在 盐酸 、 aluminum (III) chloride 、 乙醇 、 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 11.17h， 生成 ethyl 5-amino-3-methylbenzofuran-2-carboxylate hydrochloride
  参考文献：
  名称：

  新型苯并呋喃磺酰胺衍生物的合成，抗增殖活性及体外生物学评价

  摘要：

  在基于细胞的新型抗增殖剂筛选中，带有苯并呋喃磺酰胺支架的命中化合物1a对一组肿瘤细胞系表现出广谱抗增殖活性。有前景的1a体外抗增殖活性和结构新颖性促使我们研究1a的5种类似物的合成并测试其抗增殖活性。最有效的类似物1h与亲本1a相比具有增强的抗增殖活性，对NCI-H460细胞的IC 50值为4.13μM，而阳性对照为顺铂4.52μM。流式细胞仪分析显示1h在低微摩尔浓度下体外诱导NCI-H460细胞中显着水平的细胞凋亡。这些结果表明1a及其基于其苯并呋喃磺酰胺支架的类似物可能构成一类新型的抗增殖剂，值得进一步研究。

  DOI：

  10.1016/j.bmcl.2011.07.007

文献信息

• Benzoxazepinones and their use as squalene synthase inhibitors
  申请人：——

  公开号：US20030078251A1

  公开（公告）日：2003-04-24

  There is disclosed a compound represented by the formula [I]: 1 wherein R 1 is optionally substituted 1-carboxyethyl group, optionally substituted alkyl-sulfonyl group, optionally substituted (carboxy-cycloalkyl)-alkyl group, —X 1 —X 2 —Ar—X 3 —X 4 —COOH (wherein X 1 and X 4 are a bond or alkylene group, X 2 and X 3 are a bond, —O—, —S—, Ar is divalent aromatic group etc.), R 2 is alkyl group optionally substituted with alkanoyloxy group and/or hydroxy group, R 3 is alkyl group, and W is halogen atom, etc., or a salt thereof. The compound has the cholesterol lowering activity and the triglyceride lowering activity and is useful for preventing and/or treating hyperlipidemia.

  披露了一种由公式[I]表示的化合物： 1 其中R 1 是可选地取代的1-羧乙基，可选地取代的烷基亚磺酰基，可选地取代的(羧基环烷基)-烷基，—X 1 —X 2 —Ar—X 3 —X 4 —COOH(其中X 1 和X 4 是键或亚烷基，X 2 和X 3 是键，—O—，—S—，Ar是二价芳香族等)，R 2 是可选地由酰氧基和/或羟基取代的烷基，R 3 是烷基，W是卤素原子等，或其盐。该化合物具有降低胆固醇活性和降低甘油三酯活性，用于预防或治疗高脂血症。
• Synthesis and evaluation of N -(benzofuran-5-yl)aromaticsulfonamide derivatives as novel HIF-1 inhibitors that possess anti-angiogenic potential
  作者：Jinlian Wei、Yingrui Yang、Yali Li、Xiaofei Mo、Xiaoke Guo、Xiaojin Zhang、Xiaoli Xu、Zhengyu Jiang、Qidong You

  DOI：10.1016/j.bmc.2016.06.021

  日期：2017.3

  (HIF-1) as a key mediator in tumor metastasis, angiogenesis, and poor patient prognosis has been recognized as an important cancer drug target. A novel series of N-(benzofuran-5-yl)aromaticsulfonamide derivatives were synthesized and evaluated as HIF-1 inhibitor. Among these compounds, 7q exhibited specific inhibitory effects on HIF-1 by downregulating the expression of HIF-1α under hypoxic conditions

  缺氧诱导因子-1（HIF-1）作为肿瘤转移，血管生成和患者预后不良的关键介质，已被认为是重要的抗癌药物。合成了一系列新的N-（苯并呋喃-5-基）芳族磺酰胺衍生物，并将其评估为HIF-1抑制剂。在这些化合物中，7q通过在缺氧条件下下调HIF-1α的表达对HIF-1表现出特异性抑制作用。它抑制了MCF-7细胞中HIF-1的转录活性（IC50 = 12.5±0.7μM）和VEGF的分泌（IC50 =18.8μM）。同时，它还以无毒浓度显着抑制了缺氧诱导的HUVEC细胞迁移。另外，管形成试验证明了其抗血管生成活性。最后，体内研究表明化合物7q可以延缓CAM模型中的血管生成。
• BENZOXAZEPINONES AND THEIR USE AS SQUALENE SYNTHASE INHIBITORS
  申请人：Takeda Chemical Industries, Ltd.

  公开号：EP1292585A1

  公开（公告）日：2003-03-19
• [EN] BENZOXAZEPINONES AND THEIR USE AS SQUALENE SYNTHASE INHIBITORS<br/>[FR] BENZOXAZEPINONES ET LEUR UTILISATION COMME INHIBITEURS DE LA SQUALENE SYNTHASE
  申请人：TAKEDA CHEMICAL INDUSTRIES LTD

  公开号：WO2001098282A1

  公开（公告）日：2001-12-27

  There is disclosed a compound represented by formula (I), wherein R1 is optionally substituted 1-carboxyethyl group, optionally substituted alkyl-sulfonyl group, optionally substituted (carboxy-cycloalkyl)-alkyl group, -X?1-X2-Ar-X3-X4¿-COOH (wherein X?1 and X4¿ are a bond or alkylene group, X?2 and X3¿ are a bond, -O-, -S-, Ar is divalent aromatic group , etc.), R2 is alkyl group optionally substituted with alkanoyloxy group and/or hydroxy group, R3 is alkyl group, and W is halogen atom, etc., or a salt thereof. The compound has the cholesterol lowering activity and the triglyceride lowering activity and is useful for preventing and/or treating hyperlipidemia.
• Synthesis, antiproliferative activities and in vitro biological evaluation of novel benzofuransulfonamide derivatives
  作者：Li Yang、Hua Lei、Cheng-Gen Mi、Huan Liu、Tian Zhou、Ying-Lan Zhao、Xiao-Yun Lai、Zi-Cheng Li、Hang Song、Wen-Cai Huang

  DOI：10.1016/j.bmcl.2011.07.007

  日期：2011.9

  exhibited broad-spectrum antiproliferative activities against a panel of tumor cell lines. The promising in vitro antiproliferative activity and structural novelty of 1a prompted us to investigate the synthesis of five analogs of 1a and test their antiproliferative activities. The most potent analogue, 1h, exhibited enhanced antiproliferative activities compared with the parent 1a, and exhibited an

  在基于细胞的新型抗增殖剂筛选中，带有苯并呋喃磺酰胺支架的命中化合物1a对一组肿瘤细胞系表现出广谱抗增殖活性。有前景的1a体外抗增殖活性和结构新颖性促使我们研究1a的5种类似物的合成并测试其抗增殖活性。最有效的类似物1h与亲本1a相比具有增强的抗增殖活性，对NCI-H460细胞的IC 50值为4.13μM，而阳性对照为顺铂4.52μM。流式细胞仪分析显示1h在低微摩尔浓度下体外诱导NCI-H460细胞中显着水平的细胞凋亡。这些结果表明1a及其基于其苯并呋喃磺酰胺支架的类似物可能构成一类新型的抗增殖剂，值得进一步研究。