5-methylthio-2,1,3-benzoxadiazole | 53439-76-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶二唑类
• 英文名称: 5-methylthio-2,1,3-benzoxadiazole
• 英文别名: 5-methylsulfanyl-benzo[1,2,5]oxadiazole；5-Methylthio-benzofurazan；5-Thiomethoxybenzofurazan；5-Methylthiobenzofurazan；5-(Methylsulfanyl)-2,1,3-benzoxadiazole；5-methylsulfanyl-2,1,3-benzoxadiazole
• CAS: 53439-76-2
• 化学式: C₇H₆N₂OS
• 分子量: 166.203
• InChiKey: RKFNOBHSQRGFDK-UHFFFAOYSA-N

物化性质

• 沸点：
  276.9±32.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  64.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  6-fluorobenzofuroxan 在 三苯基膦 作用下， 以 水 、 氯苯 、 乙腈 为溶剂， 反应 0.83h， 生成 5-methylthio-2,1,3-benzoxadiazole
  参考文献：
  名称：

  Photophysical study of 5-substituted benzofurazan compounds as fluorogenic probes

  摘要：

  合成了九种5-取代苯并呋喃噁唑，包括未取代的苯并呋喃噁唑，并进行了荧光、光解、瞬态吸收和时间分辨热透镜信号的测量，以了解这些化合物的弛豫过程。结果表明，主要的弛豫过程是从激发单态的光反应，在激发态中主要键断裂的速率趋向于在S2←S0吸收带与S1←S0吸收带相近的化合物中增加。这些结果表明，反应态可能是S2态，并且S1态与S2态之间的相互作用促进了光反应。S1态与S2态的分离降低了光反应的速率，导致Φf值的增加。将环己烷和乙腈中5-取代苯并呋喃噁唑的Φf值与通过AM1（激发态）和AM1-CAS/CI（CI=6）相结合进行几何优化和能量水平计算得到的ΔE(S1, S2)（S1态与S2态之间的能量差）值进行了比较。ΔE(S1, S2)值与每种溶剂中的Φf值之间具有良好的相关性，从而使我们能够根据5-取代苯并呋喃噁唑的化学结构预测其荧光性质。

  DOI：

  10.1039/b202367a

文献信息

• INHIBITORS OF INDOLEAMINE 2,3-DIOXYGENASE AND METHODS OF THEIR USE
  申请人：BRISTOL-MYERS SQUIBB COMPANY

  公开号：US20200069646A1

  公开（公告）日：2020-03-05

  There are disclosed compounds that modulate or inhibit the enzymatic activity of indoleamine 2,3-dioxygenase (IDO), pharmaceutical compositions containing said compounds and methods of treating proliferative disorders, such as cancer, viral infections and/or inflammatory disorders utilizing the compounds of the disclosure.

  披露了调节或抑制吲哚胺2,3-双加氧酶（IDO）酶活性的化合物，包含所述化合物的药物组合物以及使用本披露的化合物治疗增殖性疾病的方法，如癌症、病毒感染和/或炎症性疾病。
• Inhibitors of indoleamine 2,3-dioxygenase and methods of their use
  申请人：BRISTOL-MYERS SQUIBB COMPANY

  公开号：US10959986B2

  公开（公告）日：2021-03-30

  There are disclosed compounds that modulate or inhibit the enzymatic activity of indoleamine 2,3-dioxygenase (IDO), pharmaceutical compositions containing said compounds and methods of treating proliferative disorders, such as cancer, viral infections and/or inflammatory disorders utilizing the compounds of the disclosure.

  本文公开了调节或抑制吲哚胺-2,3-二氧化酶（IDO）酶活性的化合物、含有上述化合物的药物组合物以及利用本公开化合物治疗增殖性疾病（如癌症、病毒感染和/或炎症性疾病）的方法。
• US9777002B2
  申请人：——

  公开号：US9777002B2

  公开（公告）日：2017-10-03
• Photophysical study of 5-substituted benzofurazan compounds as fluorogenic probes
  作者：Seiichi Uchiyama、Kazuyuki Takehira、Shigeru Kohtani、Tomofumi Santa、Ryoichi Nakagaki、Seiji Tobita、Kazuhiro Imai

  DOI：10.1039/b202367a

  日期：2002.9.6

  Nine 5-substituted benzofurazans including the non-substituted benzofurazan were synthesized, and measurements of the fluorescence, photolysis, transient absorption, and time-resolved thermal lensing signal were performed in order to understand the relaxation processes of these compounds. The results indicated that the main relaxation process was a photoreaction from an excited singlet state and the rate of the primary bond cleavage in the excited state tended to increase in the compound in which the S2 ← S0 absorption band is located close to the S1 ← S0 absorption band. These results suggest that the reactive state might be the S2 state, and that the interaction between the S1 and S2 states promotes the photoreaction. The separation of the S1 state from the S2 state decreases the rate of photoreaction, resulting in an increase in the Φf values. The Φf values of the 5-substituted benzofurazans in cyclohexane and acetonitrile were compared with their ΔE(S1, S2) (energy gap between the S1 and S2 states) values calculated by using a combination of AM1(EXCITED) and AM1-CAS/CI(CI = 6) for geometric optimization and calculation of the energy levels, respectively. The ΔE(S1, S2) values correlated well with the Φf values in each solvent, thus enabling us to predict the fluorescence properties of the 5-substituted benzofurazans based on their chemical structures.

  合成了九种5-取代苯并呋喃噁唑，包括未取代的苯并呋喃噁唑，并进行了荧光、光解、瞬态吸收和时间分辨热透镜信号的测量，以了解这些化合物的弛豫过程。结果表明，主要的弛豫过程是从激发单态的光反应，在激发态中主要键断裂的速率趋向于在S2←S0吸收带与S1←S0吸收带相近的化合物中增加。这些结果表明，反应态可能是S2态，并且S1态与S2态之间的相互作用促进了光反应。S1态与S2态的分离降低了光反应的速率，导致Φf值的增加。将环己烷和乙腈中5-取代苯并呋喃噁唑的Φf值与通过AM1（激发态）和AM1-CAS/CI（CI=6）相结合进行几何优化和能量水平计算得到的ΔE(S1, S2)（S1态与S2态之间的能量差）值进行了比较。ΔE(S1, S2)值与每种溶剂中的Φf值之间具有良好的相关性，从而使我们能够根据5-取代苯并呋喃噁唑的化学结构预测其荧光性质。