5-bromo-N-hydroxy-thiophene-2-carboxamide | 892387-29-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: 5-bromo-N-hydroxy-thiophene-2-carboxamide
• 英文别名: 5-bromo-N'-hydroxythiophene-2-carboximidamide
• CAS: 892387-29-0
• 化学式: C₅H₅BrN₂OS
• mdl: MFCD11179479
• 分子量: 221.077
• InChiKey: HCORWIKGUAIWEX-UHFFFAOYSA-N

物化性质

• 沸点：
  312.6±52.0 °C(Predicted)
• 密度：
  2.00±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  86.8
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-bromo-N-hydroxy-thiophene-2-carboxamide 在 bis-triphenylphosphine-palladium(II) chloride 、 sodium acetate 、 potassium carbonate 、 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 1,4-二氧六环 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 14.5h， 生成 5-(1H-indol-3-ylmethyl)-3-[5-(4-propoxyphenyl)thiophen-2-yl]-1,2,4-oxadiazole
  参考文献：
  名称：

  Design, synthesis and in vitro activity of phidianidine B derivatives as novel PTP1B inhibitors with specific selectivity

  摘要：

  A series of phidianidine B derivatives were synthesized by introducing various heterocyclic rings. Their inhibitory effects on PTP1B and other PTPs (TCPTP, SHP1, SHP2 and LAR) were evaluated. A majority of them displayed significant inhibitory potency and specific selectivity over PTP1B. The SAR and molecular docking analysis were also described. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.12.097
• 作为产物：
  描述：

  5-溴噻吩-2-甲腈 在 盐酸羟胺 、 sodium carbonate 作用下， 以 乙醇 为溶剂， 生成 5-bromo-N-hydroxy-thiophene-2-carboxamide
  参考文献：
  名称：

  通过Rh（III）催化恶二唑与烯丙醇级联反应合成功能化的茚衍生物

  摘要：

  通过CH活化/分子内羟醛缩合反应已实现了新型功能化茚衍生物的高效铑（III）催化合成。该级联反应是一种原子经济的方案，可以进一步应用于构建更复杂的化合物。

  DOI：

  10.1002/adsc.201801606

文献信息

• Nicotinic Acetylcholine Receptor Ligands
  申请人：Jacobs Robert

  公开号：US20080103170A1

  公开（公告）日：2008-05-01

  Acetylcholine receptor ligands of formula I wherein D, E and G are as described in the specification, diastereoisomers, enantiomers, pharmaceutically-acceptable salts, methods of making, pharmaceutical compositions containing, and methods for using the same.

  公式I的乙酰胆碱受体配体，其中D、E和G如说明书所述，包括对映异构体、对映体、药学上可接受的盐，制备方法，含有药物的制剂组合物以及使用方法。
• [EN] OXADIAZOLYL DIHYDROPYRANO[2,3-b]PYRIDINE INHIBITORS OF HIPK2 FOR TREATING KIDNEY FIBROSIS<br/>[FR] INHIBITEURS D'OXADIAZOLYL DIHYDROPYRANO[2,3-B] PYRIDINE DE HIPK2 POUR LE TRAITEMENT DE LA FIBROSE RÉNALE
  申请人：ICAHN SCHOOL MED MOUNT SINAI

  公开号：WO2022173795A1

  公开（公告）日：2022-08-18

  Compounds that are selective inhibitors of Smad3 activation are disclosed. The compounds are (3-aryl-1,2,4-oxadiazol-5-yl)-3,4-dihydro-2H-pyrano[2,3-b]pyridines of structure (I), in which Ar is aryl or heteroaryl. The compounds disclosed are useful in treatment of fibrotic disease, particularly renal fibrosis, and similar diseases associated with the dysregulation of the HIPK2/Smad3 signaling pathway.

  本文揭示了一种选择性抑制Smad3激活的化合物。这些化合物是结构式(I)中的(3-芳基-1,2,4-噁二唑-5-基)-3,4-二氢-2H-吡喃[2,3-b]吡啶，其中Ar是芳基或杂环芳基。所揭示的这些化合物在治疗纤维化疾病，特别是肾脏纤维化以及与HIPK2/Smad3信号通路失调相关的类似疾病中具有用途。
• WO2006/65217
  申请人：——

  公开号：——

  公开（公告）日：——
• Synthesis and biological evaluation of novel marine-derived indole-based 1,2,4-oxadiazoles derivatives as multifunctional neuroprotective agents
  作者：Cheng-Shi Jiang、Yan Fu、Li Zhang、Jing-Xu Gong、Zhen-Zhong Wang、Wei Xiao、Hai-Yan Zhang、Yue-Wei Guo

  DOI：10.1016/j.bmcl.2014.11.068

  日期：2015.1

  Phidianidines (1), isolated from the marine opisthobranch mollusk Phidiana militaris, present the first example of natural products possessing an 1,2,4-oxadiazole ring system and show various bioactivities. However, the structure-activity relationship study related to 1 has not been reported yet. As our ongoing effect toward marine-derived potential neuroprotective agents, a series of phidianidine-based derivatives have been synthesized and evaluated for neuroprotective effects against amyloid-beta(25-35) (A beta(25-35))-, hydrogenperoxide (H2O2)-, and oxygen-glucose deprivation (OGD)-induced neurotoxicity in SH-SY5Y cells. The bioassay results indicated that some of analogs, especially 2q and 2r, exhibited good in vitro neuroprotective effects in the above three screening models. The preliminary SAR study indicated that substituent groups introduced to the benzene ring play a crucial role in their bioactivity. In particular, the linear alkoxy group at 4-position favors the neuroprotective activity, while a bulky group could lead the activity decrease or loss. These findings could provide an alternative strategy for the development of novel indole-based 1,2,4-oxadiazole derivatives for the treatment of Alzheimer's disease. (C) 2014 Elsevier Ltd. All rights reserved.