ethyl 4-(bromomethyl)-1,2,3-thiadiazole-5-carboxylate | 59944-59-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: ethyl 4-(bromomethyl)-1,2,3-thiadiazole-5-carboxylate
• 英文别名: 4-bromomethyl-5-carbethoxy-1,2,3-thiadiazole；4-bromomethyl-[1,2,3]thiadiazole-5-carboxylic acid ethyl ester；ethyl 4-(bromomethyl)thiadiazole-5-carboxylate
• CAS: 59944-59-1
• 化学式: C₆H₇BrN₂O₂S
• 分子量: 251.104
• InChiKey: GJEPQLQQDJZKNJ-UHFFFAOYSA-N

物化性质

• 沸点：
  120-122 °C(Press: 2 Torr)
• 密度：
  1.682±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  80.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 4-(bromomethyl)-1,2,3-thiadiazole-5-carboxylate 在 二甲基亚砜 作用下， 反应 3.0h， 以0.4 g的产率得到5-ethoxycarbonyl-4-formyl-1,2,3-thiadiazole
  参考文献：
  名称：

  Heteroarylnitrones as Drugs for Neurodegenerative Diseases: Synthesis, Neuroprotective Properties, and Free Radical Scavenger Properties

  摘要：

  New 1,2,4-thiadiazolylnitrones and furoxanylnitrones were developed and evaluated as neuroprotective agents on a human neuroblastoma (SH-SY5Y) cells model. They inhibited at low micromolar concentrations the oxidative damage and the death induced by exposure to hydrogen peroxide. These heteroarylnitrones showed excellent peroxyl free radical absorbance capacities, analyzed by oxygen radical absorbance capacity (ORAC) assay with fluorescein as the fluorescent probe, ranging from 1.5- to 16.5-fold the value of the reference nitrone, alpha-phenyl-N-tert-butylnitrone (PBN). The electron spin resonance spectroscopy (ESR) demonstrated the ability of these derivatives to directly trap and stabilize oxygen, carbon, and sulfur-centered free radicals. These results demonstrated the potential use of these heteroarylnitrones as neuroprotective agents in preventing the death of cells exposed to enhanced oxidative stress and damage.

  DOI：

  10.1021/jm8006432
• 作为产物：
  描述：

  4-甲基-1,2,3-噻重氮-5-羧酸乙酯 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 5.0h， 生成 ethyl 4-(bromomethyl)-1,2,3-thiadiazole-5-carboxylate
  参考文献：
  名称：

  Synthesis, bioactivity and DFT structure–activity relationship study of novel 1,2,3-thiadiazole derivatives

  摘要：

  设计并合成了一系列新型 1,2,3-噻二唑衍生物。通过 1H NMR、MS 和 HRMS 对它们的结构进行了表征。生物活性测试表明，化合物 9b 具有良好的 KARI 抑制率，其中一些新型化合物还对甘蓝菜具有中等程度的除草活性。

  DOI：

  10.1007/s11164-012-0521-1

文献信息

• Pyrazolo[3,4-b]pyridine compounds, and their use as a PDE4 inhibitors
  申请人：Edlin Christopher David

  公开号：US20090131431A1

  公开（公告）日：2009-05-21

  The invention provides a compound of formula (I) or a salt thereof: wherein R 2 is H, C 1-3 alkyl, n-butyl, C 1-2 fluoroalkyl, cyclopropyl, cyclobutyl, (cyclopropyl)methyl-, —CN, or —CH 2 OH; R 3 is inter alia optionally substituted C 4-7 cycloalkyl or an optionally substituted heterocyclic group (aa), (bb) or (cc); R a is H, methyl or ethyl; R b is H or methyl; R 4 is H, methyl, ethyl, n-propyl, —C(O)-Me, or —C(O)—C 1 fluoroalkyl; and R 5 is: —C(O)—(CH 2 ) n —Ar, —C(O)-Het, —C(O)—C 1-6 alkyl, —C(O)—C 1 fluoroalkyl, —C(O)—(CH 2 ) 2 —C(O)—NR 15b NR 15b , —C(O)—CH 2 —C(O)—NR 15b NR 15b , —C(O)—NR 15b —(CH 2 )m 1 —Ar, —C(O)—NR 15b —Het, —C(O)—NR 15b —C 1-6 alkyl, —C(O)—NR 5a R 5b , —S(O) 2 —(CH 2 ) m 2 —Ar, —S(O) 2 -Het, —S(O) 2 —C 1-6 alkyl, or —CH 2 —Ar; or R 4 and R 5 taken together are —(CH 2 ) p 1 —, —(CH 2 ) 2 —X 5 —(CH 2 ) 2 —, —C(O)—(CH 2 ) p 2 —, —C(O)—N(R 15 )—(CH 2 ) p 3 —; or NR 4 R 5 is of sub-formula (y), (y1), (y2) or (y3). The invention provides the use of the compounds as inhibitors of phosphodiesterase type IV (PDE4) and/or for the treatment and/or prophylaxis of inflammatory and/or allergic diseases such as COPD and the like.

  该发明提供了化合物的结构式(I)或其盐：其中R2为H、C1-3烷基、正丁基、C1-2氟烷基、环丙基、环丁基、(环丙基)甲基、—CN或—CH2OH；R3为可选择地取代的C4-7环烷基或可选择地取代的杂环基(aa)、(bb)或(cc)；R为H、甲基或乙基；R为H或甲基；R为H、甲基、乙基、正丙基、—C(O)-甲基或—C(O)—C1氟烷基；以及R为：—C(O)—(CH2)n—Ar、—C(O)-Het、—C(O)—C1-6烷基、—C(O)—C1氟烷基、—C(O)—(CH2)2—C(O)—NR15bNR15b、—C(O)—CH2—C(O)—NR15bNR15b、—C(O)—NR15b—(CH2)m1—Ar、—C(O)—NR15b—Het、—C(O)—NR15b—C1-6烷基、—C(O)—NR5aR5b、—S(O)2—(CH2)m2—Ar、—S(O)2-Het、—S(O)2—C1-6烷基或—CH2—Ar；或R和R5一起为—(CH2)p1—、—(CH2)2—X5—(CH2)2—、—C(O)—(CH2)p2—、—C(O)—N(R15)—(CH2)p3—；或NR4R5为子式(y)、(y1)、(y2)或(y3)。该发明提供了这些化合物作为磷酸二酯酶IV型(PDE4)的抑制剂以及用于治疗和/或预防炎症和/或过敏性疾病，如慢性阻塞性肺病(COPD)等的用途。
• 5A5B6C Tricyclic spirolactone derivative, preparation method therefor and use thereof
  申请人：NANKAI UNIVERSITY

  公开号：US20210289783A1

  公开（公告）日：2021-09-23

  A 5 A 5 B 6 C tricyclic spironolactone derivative is provided with a formula XI: The present invention also relates to its preparation method and its applications in the areas of insecticide, nematicide, fungicide and anti-viral agent. The 5 A 5 B 6 C tricyclic spironolactone derivatives in the present invention are high-performance, broad-spectrum, low-toxicity and low-ecological risk compounds with a wide range of applications in the areas of agriculture, horticulture, forestry and health.

  本发明提供了一种具有XI式的5A5B6环三环螺内酯衍生物。本发明还涉及其制备方法以及在杀虫剂、线虫杀剂、杀菌剂和抗病毒剂领域的应用。本发明中的5A5B6环三环螺内酯衍生物是高性能、广谱、低毒性和低生态风险化合物，具有广泛的应用范围，可用于农业、园艺、林业和健康领域。
• α-amino acrylate microbicide, and preparation method therefor and uses thereof
  申请人：NANKAI UNIVERSITY

  公开号：US11166460B2

  公开（公告）日：2021-11-09

  The present invention relates to a microbicidal α-amino acrylic derivative and its preparation method and applications. Based on the principle of pesticide molecular design, the structural reform of the agricultural anti-plant virus activity is carried on lead compounds having the medical anti-coronavirus activity, and a series of α-amino acrylic derivatives are designed and synthesized, and in particular, α-amino acrylic derivatives containing piperidine rings are synthesized, and the systematic biological activity screening is carried by using known compounds as positive control compounds, which provide many effective anti-virus leading molecules for the preparation of pesticides, and has positive significance to reduce the pesticide application dosage and protect the environment and ecology.

  本发明涉及一种杀微生物的α-氨基丙烯酸衍生物及其制备方法和应用。根据农药分子设计原理，对具有医用抗柯洛病毒活性的先导化合物进行农业抗植物病毒活性的结构改造，设计合成了一系列α-氨基丙烯酸衍生物，特别是合成了含有哌啶环的α-氨基丙烯酸衍生物、并以已知化合物为阳性对照化合物进行了系统的生物活性筛选，为农药制备提供了多种有效的抗病毒先导分子，对减少农药用量、保护环境和生态具有积极意义。
• WO2007/36733
  申请人：——

  公开号：——

  公开（公告）日：——
• Shafiee,A., Journal of Heterocyclic Chemistry, 1976, vol. 13, p. 301 - 304
  作者：Shafiee,A.

  DOI：——

  日期：——