2-氨基-3-(4-溴苯酰基)噻吩 | 399043-24-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-氨基-3-(4-溴苯酰基)噻吩
• 中文别名: 2-氨基-3-(4-溴苄唑)噻吩
• 英文名称: (2-Amino-thiophen-3-yl)-(4-bromo-phenyl)-methanone
• 英文别名: 2-Amino-3-(4-bromobenzoyl)thiophene；(2-aminothiophen-3-yl)-(4-bromophenyl)methanone
• CAS: 399043-24-4
• 化学式: C₁₁H₈BrNOS
• 分子量: 282.161
• InChiKey: UEAXJDFGNXSVSK-UHFFFAOYSA-N

物化性质

• 熔点：
  180-184 °C(lit.)
• 沸点：
  446.1±35.0 °C(Predicted)
• 密度：
  1.607±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  71.3
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xn
• 安全说明：
  S26,S36/37/39
• 危险类别码：
  R22,R36/37/38,R43
• 海关编码：
  2934999090
• WGK Germany：
  3

反应信息

• 作为反应物：
  描述：

  2-氨基-3-(4-溴苯酰基)噻吩 在 哌啶 、 potassium hydroxide 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.13h， 生成
  参考文献：
  名称：

  [EN] GLUN2 SUBUNIT SELECTIVE ANTAGONISTS OF THE N-METHYL-D-ASPARTATE RECEPTORS
  [FR] ANTAGONISTES SÉLECTIFS DE LA SOUS-UNITÉ GLUN2 DES RÉCEPTEURS DU N-MÉTHYL-D-ASPARTATE

  摘要：

  Compounds that selectively inhibit the GluN2 subunits of NMDA receptors are disclosed. In general, the compounds have superior activity against GluN2C/D subunit(s) over GluN2A/B subunit(s). Optionally, the compounds have a structure of Formulas (I), (II), (III), or other formulas disclosed herein, enantiomers or diastereomers thereof, or pharmaceutically acceptable salts thereof. Pharmaceutical formulations containing one or more of the compounds are also disclosed. Additionally, methods of treating a neurological condition or disorder using the compounds or their pharmaceutical formulations thereof are disclosed. Exemplary neurological conditions or disorders include Parkinson's disease, dystonia and related motor disorders, depression, neuropsychiatric indications, stoke, hypoxia, traumatic brain injury, acute injuries involving the white matter, Alzheimer's disease, compulsivity and related disorders, and epilepsy.

  公开号：

  WO2022226161A1
• 作为产物：
  描述：

  1,4-二硫-2,5-二醇 、 4-溴苯甲酰乙腈 在 二乙胺 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以41%的产率得到2-氨基-3-(4-溴苯酰基)噻吩
  参考文献：
  名称：

  2-Amino-3-aroyl-4,5-alkylthiophenes:  Agonist Allosteric Enhancers at Human A₁ Adenosine Receptors

  摘要：

  2-Amino-3-benzoylthiophenes are allosteric enhancers (AE) of agonist activity at the A(1) adenosine receptor. The present report describes syntheses and assays of the AE activity at the human A(1)AR (hA(1)AR) of a panel of compounds consisting of nine 2-amino-3-aroylthiophenes (3a-i), eight 2-amino-3-benzoyl-4,5-dimethylthiophenes (12a-h), three 3-aroyl-2-carboxy-4,5-dimethylthiophenes (15a-c), 10 2-amino-3-benzoyl-5,6-dihydro-4H-cyclopenta[b]thiophenes (17a-j), 14 2-amino-3-benzoyl-4,5,6,7-tetrahydrobenzo[b]thiophenes (18a-n), and 15 2-amino-3-benzoyl-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophenes (19a-o). An in vitro assay employing the A(1)AR agonist [I-125]ABA and membranes from CHO-K1 cells stably expressing the hA(1)AR measured, as an index of AE activity, the ability of a candidate AE to stabilize the agonist-A(1)AR-G protein ternary complex. Compounds 3a-i had little or no AE activity, and compounds 12a-h had only modest activity, evidence that AE activity depended absolutely on the presence of at least a methyl group at C-4 and C-5. Compounds 17a-c lacked AE activity, suggesting the 2-amino group is essential. Polymethylene bridges linked thiophene C-4 and C-5 of compounds 17a-j, 18a-n, and 19a-o. AE activity increased with the size of the -(CH2)(n)- bridge, n = 3 < n = 4 < n = 5. The 3-carbethoxy substituents of 17a, 18a, and 19a did not support AE activity, but a 3-aroyl group did. Bulky (or hydrophobic) substituents at the meta and para positions of the 3-benzoyl group and also 3-naphthoyl groups greatly enhanced activity. Thus, the hA(1)AR contains an allosteric binding site able to accommodate 3-aroyl substituents that are bulky and/or hydrophobic but not necessarily planar. A second region in the allosteric binding site interacts constructively with alkyl substituents at thiophene C-4 and/or C-5.

  DOI：

  10.1021/jm010081p

文献信息

• METHODS OF TREATING A BOTULINUM TOXIN RELATED CONDITION IN A SUBJECT
  申请人：Jacobson Alan

  公开号：US20110190285A1

  公开（公告）日：2011-08-04

  The present invention provides methods of treating a botulinum toxin related condition in a subject. In certain embodiments, the methods involve administering a compound of the following formulas: (I), (II), (III), (IV), (V).

  本发明提供了治疗受体肉毒毒素相关疾病的方法。在某些实施例中，该方法涉及到给受体注射以下化合物：(I)、(II)、(III)、(IV)、(V)。
• COMPOUNDS AND METHODS FOR TREATING ZINC MATRIX METALLOPROTEASE DEPENDENT DISEASES
  申请人：Jacobson Alan

  公开号：US20110034521A1

  公开（公告）日：2011-02-10

  The present invention provides compounds and methods for treating zinc matrix metalloprotease dependent diseases. In certain embodiments, the compounds of the present invention have the following formulas:

  本发明提供了化合物和治疗锌基金属蛋白酶依赖性疾病的方法。在某些实施例中，本发明的化合物具有以下结构式：