(5-碘-噻吩-2-基)-甲醇 | 13781-27-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 中文名称: (5-碘-噻吩-2-基)-甲醇
• 英文名称: 2-Hydroxymethyl-5-iodothiophene
• 英文别名: (5-iodothiophen-2-yl)methanol；5-iodo-2-thiophenemethanol；5-iodothenyl alcohol
• CAS: 13781-27-6
• 化学式: C₅H₅IOS
• 分子量: 240.065
• InChiKey: VTPZGZASDXXIQL-UHFFFAOYSA-N

物化性质

• 沸点：
  291.8±30.0 °C(Predicted)
• 密度：
  2.091±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  48.5
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  (5-碘-噻吩-2-基)-甲醇 以 N,N-二甲基甲酰胺 为溶剂， 生成 2,2'-bithiophene-5,5'-diyldimethanol
  参考文献：
  名称：

  Polythiophene anti-tumor agents

  摘要：

  描述了作为抗肿瘤药剂有用的新型聚噻吩化合物。所述的优选化合物的化学式为：其中n为0-2，R.sub.2和R.sub.3为可选择取代的2-噻吩基或3-噻吩基，已发现具有对转化的人类细胞具有选择性细胞毒活性。含有所述聚噻吩化合物的药物组合物预计在肿瘤细胞系实验基础上对慢性生长的肿瘤具有良好的化疗活性。还描述了一种利用所披露的聚噻吩化合物治疗患有肿瘤的患者的方法。

  公开号：

  US05578636A1
• 作为产物：
  描述：

  2-噻吩甲醇 在 N-碘代丁二酰亚胺 、 对甲苯磺酸 作用下， 以 乙醇 为溶剂， 反应 0.17h， 以98%的产率得到(5-碘-噻吩-2-基)-甲醇
  参考文献：
  名称：

  噻吩衍生物的清洁高效碘化

  摘要：

  摘要 噻吩衍生物的碘化是通过简单，快速和有效的方法实现的。噻吩和2-或3-取代或3,4-二取代的噻吩在乙醇中用4-甲苯磺酸活化的N-碘琥珀酰亚胺（NIS）进行碘化，得到纯碘化产物，无需进一步纯化。 噻吩衍生物的碘化是通过简单，快速和有效的方法实现的。噻吩和2-或3-取代或3,4-二取代的噻吩在乙醇中用4-甲苯磺酸活化的N-碘琥珀酰亚胺（NIS）进行碘化，得到纯碘化产物，无需进一步纯化。

  DOI：

  10.1055/s-0035-1560480

文献信息

• Luminescent molecular solar concentrators made of multi-Bodipy dyes
  作者：Antoine Mirloup、Pascal Retailleau、Raymond Ziessel

  DOI：10.1016/j.tetlet.2013.06.039

  日期：2013.8

  photoactive arrays consisting of Bodipy scaffoldings is described. The synthetic strategy involved first the construction of functionalised modules, then the use of specific Knoevenagel reactions. Boron-protection is required to avoid self-condensation. Comparison of thienylBodipy dyes with their phenyl analogues showed them to be both less chemically stable and more weakly fluorescent. In the multichromophoric

  描述了由Bodipy支架组成的光敏阵列的合成。合成策略首先涉及功能化模块的构建，然后使用特定的Knoevenagel反应。需要进行硼保护以避免自凝结。噻吩基二联染料与苯基类似物的比较表明，它们化学稳定性较差，荧光性较弱。在多发色物种中，以最高能量单位吸收后会发生有效的级联能量转移。根据特定参考化合物的行为分析了混合染料的氧化还原活性。
• Hydroxymethyl-polythiophene derivatives
  申请人：Industrial Technology Research Institute

  公开号：US05596014A1

  公开（公告）日：1997-01-21

  A pharmaceutical composition containing a compound and an excipient, the compound having the formula: ##STR1## in which n is 2, 3 or 4; R is H, --CH(R.sup.1).cndot.OR.sup.2, --CH(O--Z).sub.2, or --COR.sup.3 ; R.sup.1 is H, C.sub.1-6 alkyl, C.sub.2-6 alkenyl, OH, C.sub.1-6 hydroxyalkyl, or COOH; R.sup.2 is H, C.sub.1-6 alkyl, C.sub.2-6 alkenyl, tetrahydropyranyl, phenyl, benzoyl, C.sub.1-6 acyl, tosyl, or --CO--Y--COOH; and R.sup.3 is H, C.sub.1-6 alkyl, C.sub.2-6 alkenyl, OH, C.sub.1-6 hydroxyalkyl, or COOH; wherein Z is C.sub.1-6 alkyl, C.sub.2-6 alkenyl, or C.sub.1-6 acyl; and Y is C.sub.1-6 alkylidene, C.sub.2-6 alkenylidene, phenylene, or deleted; or an ester or a salt thereof.

  一种含有化合物和赋形剂的药物组合物，该化合物具有以下结构式：##STR1## 其中n为2、3或4；R为H、--CH(R.sup.1).cndot.OR.sup.2、--CH(O--Z).sub.2或--COR.sup.3；R.sup.1为H、C.sub.1-6烷基、C.sub.2-6烯基、OH、C.sub.1-6羟基烷基或COOH；R.sup.2为H、C.sub.1-6烷基、C.sub.2-6烯基、四氢吡喃基、苯基、苯甲酰基、C.sub.1-6酰基、对甲苯磺酰基或--CO--Y--COOH；R.sup.3为H、C.sub.1-6烷基、C.sub.2-6烯基、OH、C.sub.1-6羟基烷基或COOH；其中Z为C.sub.1-6烷基、C.sub.2-6烯基或C.sub.1-6酰基；Y为C.sub.1-6烷基亚甲基、C.sub.2-6烯基亚甲基、苯基亚甲基或删除；或其酯或盐。
• Hydroxymethypolythiophene derivatives
  申请人：Industrial Technology Research Institute

  公开号：US05596107A1

  公开（公告）日：1997-01-21

  Novel hydroxymethylthiophene derivatives and their medical use in treating or preventing inflammation and edema.

  新型羟甲基噻吩衍生物及其在治疗或预防炎症和水肿方面的医学用途。
• Hydroxymethylpolythiophene derivatives
  申请人：Industrial Technology Research Institute

  公开号：US05608081A1

  公开（公告）日：1997-03-04

  Novel hydroxymethylthiophene derivatives and their medical use in treating or preventing inflammation and edema.

  新型羟甲基噻吩衍生物及其在治疗或预防炎症和水肿方面的医学用途。
• Synthesis of ¹³¹I-Labeled Glucose-Conjugated Inhibitors of <i>O</i>⁶-Methylguanine-DNA Methyltransferase (MGMT) and Comparison with Nonconjugated Inhibitors as Potential Tools for in Vivo MGMT Imaging
  作者：Ute Mühlhausen、Ralf Schirrmacher、Markus Piel、Bernd Lecher、Manuela Briegert、Andrea Piee-Staffa、Bernd Kaina、Frank Rösch

  DOI：10.1021/jm050588q

  日期：2006.1.1

  O-6-Substituted guanine derivatives are powerful agents used for tumor cell sensitization by inhibition of the DNA repair enzyme O-6-methylguanine-DNA methyltransferase (MGMT). To provide targeted accumulation of MGMT inhibitors in tumor tissue as well as tools for in vivo imaging, we synthesized iodinated C-8-alkyl-linked glucose conjugates of 2-amino-6-(5-iodothenyl)-9H-purine (O-6-(5-iodothenyl) guanine, ITG) and 2-amino-6-(3-iodobenzyloxy)-9H-purine (O-6-(5-iodobenzyl) guanine, IBG). These compounds have MGMT inhibitor constants (IC50 values) of 0.8 and 0.45 mu M for ITGG and IBGG, respectively, as determined in HeLa S3 cells after 2-h incubation with inhibitor. To substantiate that the I-131-(hetero)arylmethylene group at the O-6-position of guanine is transferred to MGMT, both the glucose conjugated inhibitors ITGG and IBGG and the corresponding nonglucose conjugated compounds ITG and IBG were labeled with iodine-131. The radioiodinations of all compounds with [I-131]I- were performed with radiochemical yields of > 70% for the destannylation of the corresponding tri-n-butylstannylated precursors. The binding ability of [I-131]ITGG, [(131)]IBGG, [I-131]ITG, and [I-131]IBG to purified MGMT was tested. All radioactive compounds were substrates for MGMT, as demonstrated using a competitive repair assay. The newly synthesized radioactive inhibitors were utilized to study ex vivo biodistribution in mice, and the tumor-to-blood ratio of tissue uptake of [I-131]IBG and [I-131]IBGG was determined to be 0.24 and 0.76 after 0.5 h, respectively.