2-溴甲基-5-氯苯并呋喃 | 139313-90-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 中文名称: 2-溴甲基-5-氯苯并呋喃
• 英文名称: 2-(bromomethyl)-5-chlorobenzofuran
• 英文别名: 2-(bromomethyl)-5-chloro-1-benzofuran
• CAS: 139313-90-9
• 化学式: C₉H₆BrClO
• 分子量: 245.503
• InChiKey: YAXVJPLTIWGXJV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  13.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-溴甲基-5-氯苯并呋喃 在 吡啶 、 氢氧化钾 、 氯化亚砜 、 盐酸羟胺 、 sodium methylate 、 四丁基硫酸氢铵 作用下， 以 甲醇 、 二氯甲烷 、 氯仿 、 水 为溶剂， 反应 19.83h， 生成 4-[(5-chloro-1-benzofuran-2-yl)methyl]-5H-1,2,3,5-oxathiadiazole 2-oxide
  参考文献：
  名称：

  Antihyperglycemic activity of novel substituted 3H-1,2,3,5-oxathiadiazole 2-oxides

  摘要：

  A series of substituted 3H-1,2,3,5-oxathiadiazole-2-oxides (6) was prepared and tested for antihyperglycemic activity in the db/db mouse, a model for type 2 (non-insulin dependent) diabetes mellitus. The oxathiadiazoles 6 were synthesized by a two-step sequence: treatment of a substituted acetonitrile (4) with hydroxylamine to give the corresponding amidoxime (5) and cyclization with thionyl chloride to yield 6. In terms of potency, the 2-naphthalenylmethyl group (as in compound 3) was found to be the optimal substituent in this series. Compound 3 was approximately 5 times more potent than ciglitazone (1).

  DOI：

  10.1021/jm00085a002
• 作为产物：
  描述：

  5-氯-2-甲基苯并呋喃 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 作用下， 以 四氯化碳 为溶剂， 反应 24.0h， 生成 2-溴甲基-5-氯苯并呋喃
  参考文献：
  名称：

  Antihyperglycemic activity of novel substituted 3H-1,2,3,5-oxathiadiazole 2-oxides

  摘要：

  A series of substituted 3H-1,2,3,5-oxathiadiazole-2-oxides (6) was prepared and tested for antihyperglycemic activity in the db/db mouse, a model for type 2 (non-insulin dependent) diabetes mellitus. The oxathiadiazoles 6 were synthesized by a two-step sequence: treatment of a substituted acetonitrile (4) with hydroxylamine to give the corresponding amidoxime (5) and cyclization with thionyl chloride to yield 6. In terms of potency, the 2-naphthalenylmethyl group (as in compound 3) was found to be the optimal substituent in this series. Compound 3 was approximately 5 times more potent than ciglitazone (1).

  DOI：

  10.1021/jm00085a002

文献信息

• [EN] TREATMENT OR PROPHYLAXIS OF PROLIFERATIVE CONDITIONS<br/>[FR] TRAITEMENT OU PROPHYLAXIE D'ÉTATS PROLIFÉRATIFS
  申请人：UNIV DUNDEE

  公开号：WO2010125350A1

  公开（公告）日：2010-11-04

  The invention relates to novel compounds for use in the treatment or prophylaxis of cancers and other proliferative conditions that are for example characterized by cells that express cytochrome P450 1B1 (CYP1B1) and allelic variants thereof. The invention also provides pharmaceutical compositions comprising one or more such compounds for use in medical therapy, for example in the treatment of prophylaxis of cancers or other proliferative conditions, as well as methods for treating cancers or other conditions in human or non-human animal patients. The invention also provides methods for identifying novel compounds for use in the treatment of prophylaxis of cancers and other proliferative conditions that are for example characterized by cells that express CYP1 B1 and allelic variants thereof. The invention also provides a method for determining the efficacy of a compound of the invention in treating cancer.

  该发明涉及用于治疗或预防癌症和其他增殖性疾病的新化合物，例如这些疾病的特征是细胞表达细胞色素P450 1B1（CYP1B1）及其等位基因变体。该发明还提供包含一种或多种此类化合物的药物组合物，用于医学治疗，例如用于治疗或预防癌症或其他增殖性疾病，以及用于治疗人类或非人类动物患者的癌症或其他疾病的方法。该发明还提供用于识别用于治疗或预防癌症和其他增殖性疾病的新化合物的方法，例如这些疾病的特征是细胞表达CYP1B1及其等位基因变体。该发明还提供一种用于确定该发明中化合物治疗癌症的疗效的方法。
• Inhibition of Aromatase (P450Arom) by some 1-(Benzofuran-2-ylmethyl)imidazoles
  作者：Caroline P Owen、Paul J Nicholls、H John Smith、Rhys Whomsley

  DOI：10.1211/0022357991772637

  日期：2010.2.18

  prostatic cancer by their inhibition of 17beta-hydroxylase:17,20-lyase (P450 17), have been extended to their selectivity against placental microsomal aromatase (P450(Arom)) in man. The compounds were 3-7-fold more potent than aminoglutethimide and had some selectivity for P450 17 as expressed by the ratio (IC50 P450(Arom))/(IC50 P450) 17)/17.0 (2), 10.3 (3), 34.6 (4) and 42.0 (5), where IC50 is the concentration

  一系列1-（苯并呋喃-2-基甲基）咪唑1-5的研究先前已被扩展为通过抑制17β-羟化酶：17,20-裂合酶（P450 17）作为前列腺癌的潜在治疗药物，现已扩展到它们对人胎盘微粒体芳香化酶（P450（Arom））的选择性。该化合物的效力比氨基谷氨酰胺高3-7倍，并且对P450 17具有一定的选择性，其比率为（IC50 P450（Arom））/（IC50 P450）17）/17.0（2），10.3（3），34.6 （4）和42.0（5），其中IC50是导致50％抑制的浓度。与外消旋的α-苯基取代的化合物（6、80-1000 x氨基戊二酰亚胺）和某些外消旋的α-甲基（8.5和12.2 x氨基戊乙酰亚胺）和α-乙基（12.1）相比，P450（Arom）的1-5效力较低和32.9 x氨基戊二酰亚胺）类似物已得到合理化。
• Treatment or prophylaxis of proliferative conditions
  申请人：The University of the University of Dundee

  公开号：US08283340B2

  公开（公告）日：2012-10-09

  The disclosure relates to novel compounds for use in the treatment or prophylaxis of cancers and other proliferative conditions that are for example characterized by cells that express cytochrome P450 1B1 (CYP1B1) and allelic variants thereof. Also provided are pharmaceutical compositions comprising one or more such compounds for use in medical therapy, for example in the treatment of prophylaxis of cancers or other proliferative conditions, as well as methods for treating cancers or other conditions in human or non-human animal patients. Provided are methods for identifying novel compounds for use in the treatment of prophylaxis of cancers and other proliferative conditions that are for example characterized by cells that express CYP1B1 and allelic variants thereof. Finally, provided is a method for determining the efficacy of a compound as described herein in treating cancer.

  本公开涉及新型化合物的使用，用于治疗或预防癌症和其他增生性疾病，例如其特征为表达细胞色素P450 1B1（CYP1B1）及其等位基因变异体的细胞。还提供了包含一种或多种这样的化合物的药物组合物，用于医学治疗，例如用于治疗或预防癌症或其他增生性疾病，以及用于治疗人类或非人类动物患者的癌症或其他疾病的方法。提供了用于寻找用于治疗或预防表达CYP1B1及其等位基因变异体的细胞的癌症和其他增生性疾病的新型化合物的方法。最后，提供了一种确定本文所述化合物在治疗癌症方面的疗效的方法。
• TREATMENT OR PROPHYLAXIS OF PROLIFERATIVE CONDITIONS
  申请人：Everett Steven Albert

  公开号：US20120190639A1

  公开（公告）日：2012-07-26

  The invention relates to novel compounds for use in the treatment or prophylaxis of cancers and other proliferative conditions that are for example characterized by cells that express cytochrome P450 1B1 (CYP1B1) and allelic variants thereof. The invention also provides pharmaceutical compositions comprising one or more such compounds for use in medical therapy, for example in the treatment of prophylaxis of cancers or other proliferative conditions, as well as methods for treating cancers or other conditions in human or non-human animal patients. The invention also provides methods for identifying novel compounds for use in the treatment of prophylaxis of cancers and other proliferative conditions that are for example characterized by cells that express CYP1 B1 and allelic variants thereof. The invention also provides a method for determining the efficacy of a compound of the invention in treating cancer.

  本发明涉及新型化合物，用于治疗或预防癌症和其他增生性疾病，例如其细胞表达细胞色素P450 1B1（CYP1B1）及其等位基因变异的疾病。本发明还提供了含有一种或多种这样的化合物的制药组合物，用于医学治疗，例如治疗癌症或其他增生性疾病的预防或治疗，以及用于治疗人类或非人类动物患者的癌症或其他疾病的方法。本发明还提供用于鉴定用于治疗或预防表达CYP1B1及其等位基因变异的细胞的癌症和其他增生性疾病的新型化合物的方法。本发明还提供了一种用于确定本发明的化合物在治疗癌症方面的功效的方法。
• Design of Cell-Permeable Inhibitors of Eukaryotic Translation Initiation Factor 4E (eIF4E) for Inhibiting Aberrant Cap-Dependent Translation in Cancer
  作者：Emilio L. Cárdenas、Rachel L. O’Rourke、Arya Menon、Jennifer Meagher、Jeanne Stuckey、Amanda L. Garner

  DOI：10.1021/acs.jmedchem.3c00917

  日期：2023.8.10

  translation factor, and its activation has been shown to drive cancer initiation, progression, metastasis, and drug resistance. These findings have established eIF4E as a translational oncogene and promising, albeit challenging, anti-cancer therapeutic target. Although significant effort has been put forth toward inhibiting eIF4E, the design of cell-permeable, cap-competitive inhibitors remains a challenge

  真核翻译起始因子 4E （eIF4E） 是一种 RNA 结合蛋白，可与编码 mRNA 的 5' 末端的 m7GpppX 帽结合，以启动帽依赖性翻译。虽然所有细胞都需要帽依赖性翻译，但癌细胞对增强的翻译能力上瘾，从而驱动参与增殖、逃避细胞凋亡、转移和血管生成以及其他癌性表型的致癌蛋白的产生。eIF4E 是限速翻译因子，其激活已被证明可驱动癌症的发生、进展、转移和耐药性。这些发现已将 eIF4E 确立为一种转化癌基因和有前途但具有挑战性的抗癌治疗靶点。尽管已经为抑制 eIF4E 付出了大量努力，但可细胞渗透、帽竞争性抑制剂的设计仍然是一个挑战。在本文中，我们描述了我们为解决这一长期挑战所做的工作。通过采用无环核苷膦酸盐前药策略，我们报道了 eIF4E 结合的细胞渗透性抑制剂与加帽 mRNA 结合以抑制帽依赖性翻译的合成。