3-羟基-1-苯并噻吩-2-甲腈 | 57477-69-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 中文名称: 3-羟基-1-苯并噻吩-2-甲腈
• 英文名称: 3-hydroxy-1-benzothiophene-2-carbonitrile
• 英文别名: 3-hydroxy[1]benzothiophene-2-carbonitrile；3-hydroxybenzo[b]thiophene-2-carbonitrile；3-hydroxy-benzo[b]thiophene-2-carbonitrile；3-hydroxybenzo[b]-thiophene-2-carbonitrile；2-Cyano-3-hydroxybenzo<4.5>thiophen；2-Cyano-3-hydroxy-benzothiophen
• CAS: 57477-69-7
• 化学式: C₉H₅NOS
• mdl: MFCD00172851
• 分子量: 175.211
• InChiKey: DOXMOBZBFOKSIQ-UHFFFAOYSA-N

物化性质

• 熔点：
  173-174 °C
• 沸点：
  379.1±27.0 °C(Predicted)
• 密度：
  1.44±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  72.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-羟基-1-苯并噻吩-2-甲腈 在 偶氮二甲酸二异丙酯 、 羟胺 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 5.5h， 生成 (Z)-tert-butyl 4-((2-(N'-hydroxycarbamimidoyl)benzo[b]thiophen-3-yl)oxy)piperidine-1-carboxylate
  参考文献：
  名称：

  Design and Synthesis of High Affinity Inhibitors of Plasmodium falciparum and Plasmodium vivax N-Myristoyltransferases Directed by Ligand Efficiency Dependent Lipophilicity (LELP)

  摘要：

  N-Myristoyltransferase (NMT) is an essential eukaryotic enzyme and an attractive drug target in parasitic infections such as malaria. We have previously reported that 2-(3-(piperidin-4-yloxy)benzo[b]thiophen-2-yl)-5-((1,3,5-trimethyl-1H-pyrazol-4-yl)methyl)-1,3,4-oxadiazole (34c) is a high affinity inhibitor of both Plasmodium falciparum and P. vivax NMT and displays activity in vivo against a rodent malaria model. Here we describe the discovery of 34c through optimization of a previously described series. Development, guided by targeting a ligand efficiency dependent lipophilicity (LELP) score of less than 10, yielded a 100-fold increase in enzyme affinity and a 100-fold drop in lipophilicity with the addition of only two heavy atoms. 34c was found to be equipotent on chloroquine-sensitive and -resistant cell lines and on both blood and liver stage forms of the parasite. These data further validate NMT as an exciting drug target in malaria and support 34c as an attractive tool for further optimization.

  DOI：

  10.1021/jm500066b
• 作为产物：
  描述：

  ethyl 2-mercaptobenzoate 在 sodium hydride 、 potassium carbonate 、 potassium iodide 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 4.0h， 生成 3-羟基-1-苯并噻吩-2-甲腈
  参考文献：
  名称：

  Polycyclic N-Heterocyclic Compounds. 57 Syntheses of Fused Furo(or Thieno)[2,3-b]pyridine Derivatives via Smiles Rearrangement and Cyclization

  摘要：

  An efficient methodology for the synthesis of thieno[2,3-c][2,7] naphthyridine (6), thieno[2,3-c]isoquinoline (11), furo[2,3-c]isoquinoline (14), [1]benzothieno[3,2-d]thieno[2,3-b]pyridine (21), and [1]benzothieno[3,2-d]furo-2,3-b]pyridine (26) skeletons from 4-[o-cyanoarylthio(or oxy)]butyronitriles with base via Smiles type rearrangement reaction followed by the cyclization is described.

  DOI：

  10.3987/com-01-9168

文献信息

• Synthesis and Structure Activity Relationship Studies of Benzothieno[3,2-b]furan Derivatives as a Novel Class of IKK.BETA. Inhibitors
  作者：Hideyuki Sugiyama、Masato Yoshida、Kouji Mori、Tomohiro Kawamoto、Satoshi Sogabe、Terufumi Takagi、Hideyuki Oki、Toshimasa Tanaka、Hiroyuki Kimura、Yoshinori Ikeura

  DOI：10.1248/cpb.55.613

  日期：——

  As a novel class of IKKbeta inhibitors, a series of tricyclic furan derivatives was designed and synthesized based on the structure of known thiophene IKKbeta inhibitors. Among the various fused furan derivatives synthesized, a benzothieno[3,2-b]furan derivative 13a displayed potent inhibitory activity towards IKKbeta in enzymatic and cellular assays. The potent inhibitory activity originates from

  作为一类新型的IKKbeta抑制剂，根据已知的噻吩IKKbeta抑制剂的结构设计和合成了一系列三环呋喃衍生物。在各种合成的融合呋喃衍生物中，苯并噻吩并[3,2-b]呋喃衍生物13a在酶和细胞分析中显示出对IKKbeta的有效抑制活性。有效的抑制活性源自分子内的非键合S ... O相互作用，这已通过JNK3的16k X射线结构得到证实。在核心结构上引入其他取代基导致发现了6-烷氧基衍生物，该衍生物具有与13a相当的IKKbeta抑制活性，并具有改善的代谢稳定性。其中，发现适当的亲脂性化合物16a，h，i和13g（log D> 2）具有良好的口服生物利用度。
• Polycyclic<i>N</i>-hetero compounds.<b>XXXVIII</b>. Synthesis and evaluation of antidepressive activity of [1]benzothieno[2′,3′:4,5]furo[3,2-<i>d</i>]primidines and their precursors
  作者：Kenji Sasaki、Yohsuke Tashima、Taiji Nakayama、Takashi Hirota

  DOI：10.1002/jhet.5570280211

  日期：1991.2

  Synthesis of [1]benzothieno[2′,3′:4,5]furo[3,2-d]pyrimidines is described. Antidepressive evaluation of these compounds and their precursors were screened by inhibitory action of reserpine-induced hypothermia.

  描述了[1]苯并噻吩并[2'，3'：4,5]呋喃[3,2- d ]嘧啶的合成。通过利血平诱导的体温过低的抑制作用筛选了这些化合物及其前体的抗抑郁作用。
• Concise Synthesis of Highly Substituted Benzo[a]quinolizines by a Multicomponent Reaction/Allylation/Heck Reaction Sequence
  作者：René den Heeten、Léon J. P. van der Boon、Daniël L. J. Broere、Elwin Janssen、Frans J. J. de Kanter、Eelco Ruijter、Romano V. A. Orru

  DOI：10.1002/ejoc.201101170

  日期：2012.1

  combination of the recently developed multicomponent construction of highly substituted 3,4-dihydropyridones with subsequent allylation and intramolecular Heck-type cyclization allows the straightforward construction of benzo[a]quinolizines, a class of polycyclic compounds that – despite their interesting pharmacological and photochemical properties – have little precedent in the literature. After optimization

  最近开发的高度取代的 3,4-二氢吡啶酮的多组分结构与随后的烯丙基化和分子内 Heck 型环化相结合，可以直接构建苯并 [a] 喹啉，这是一类多环化合物，尽管它们具有有趣的药理和光化学特性– 在文献中鲜有先例。在优化各个步骤后，我们使用这个可靠的三步序列来生成一个小库，其中包含多种取代的苯并 [a] 喹嗪和各种杂环类似物。
• Analgesic compositions consisting of
  申请人：Ayerst, McKenna & Harrison Inc.

  公开号：US04431657A1

  公开（公告）日：1984-02-14

  Herein is disclosed 2H-benzothieno[3,2-c]pyrazol-3-amine derivatives, therapeutically acceptable acid addition salts thereof, processes for their preparation, methods of using the derivatives and pharmaceutical compositions. The derivatives are useful for producing analgesia in a mammal. In addition, some of the derivatives are useful for inhibiting gastric acid secretion, convulsions, anxiety and aggression, and producing muscle relaxation, hypnosis and sedation in a mammal.

  本文披露了2H-苯并噻吩[3,2-c]吡唑-3-胺衍生物及其治疗上可接受的酸盐、其制备方法、使用这些衍生物的方法和制药组合物。这些衍生物对于在哺乳动物中产生镇痛作用很有用。此外，其中一些衍生物对于抑制胃酸分泌、抗痉挛、抗焦虑和攻击性、以及在哺乳动物中产生肌肉松弛、催眠和镇静作用也很有用。
• ROYER R.; RENE L.; AUROUSSEAU M.; NICOINE F., EUR. J. MED. CHEM. CHIM. THER., 1979, 14, NO 5, 467-469
  作者：ROYER R.、 RENE L.、 AUROUSSEAU M.、 NICOINE F.

  DOI：——

  日期：——