2-((pyridin-2-ylmethyl)thio)benzo[d]oxazole | 83782-84-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶唑类
• 英文名称: 2-((pyridin-2-ylmethyl)thio)benzo[d]oxazole
• 英文别名: Benzoxazole, 2-[(2-pyridinylmethyl)thio]-；2-(pyridin-2-ylmethylsulfanyl)-1,3-benzoxazole
• CAS: 83782-84-7
• 化学式: C₁₃H₁₀N₂OS
• 分子量: 242.301
• InChiKey: XWBOXAKFPCBUDH-UHFFFAOYSA-N

物化性质

• 沸点：
  403.7±47.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 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：

  2-氯甲基吡啶盐酸盐 、 2-巯基苯并恶唑 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 4.0h， 生成 2-((pyridin-2-ylmethyl)thio)benzo[d]oxazole
  参考文献：
  名称：

  2-[(3-Pyridinylmethyl)thio]pyrimidine derivatives: New bronchosecretolytic agents

  摘要：

  2-[(3-Pyridinylmethyl)thio]pyrimidine derivatives (1a-n) promote the excretion of phenol red into the mouse trachea, indicating an increased tracheobronchial secretion. Furthermore, 2-[(3-pyridinylmethyl)thio]pyrimidine (1a) (tasuldine) produces greater excretion of phenol red into the mouse trachea after systemic administration than the known bronchosecretolytic ambroxol. Compound 1a also reduces the viscosity of canine bronchial mucus. Compound 1a has been selected for clinical investigations.

  DOI：

  10.1021/jm00386a018

文献信息

• Metal- and base-free regioselective thiolation of the methyl C(sp³)–H bond in 2-picoline <i>N</i>-oxides
  作者：Dong Wang、Zhenlin Liu、Zhentao Wang、Xinyue Ma、Peng Yu

  DOI：10.1039/c8gc03072c

  日期：——

  A one-pot, two-step synthesis of pyridine-2-ylmethyl thioethers is developed through a TFAA-mediated [3,3]-sigmatropic rearrangement of pyridine N-oxides and TBAB-catalyzed direct conversion of trifluoroacetates into thioethers under metal- and base-free conditions. This methodology enables thiolation of the unactivated methyl C(sp3)–H bond in 2-picolines with thiols. Remarkable features of the method

  通过TFAA介导的吡啶N-氧化物的[3,3]-σ重排和TBAB催化的三氟乙酸盐在金属和金属催化下直接转化为三氟乙酸的反应，可以开发一锅两步的吡啶-2-基甲基硫醚合成方法无碱条件。这种方法可以使未活化的甲基C（sp 3硫醇化）–2-甲基吡啶与硫醇的氢键。该方法的显着特征包括区域选择性高，阶跃和原子经济，条件温和，操作简单，底物范围广和可扩展性。此外，该方法已成功地用于合成奥美拉唑硫化物和雷贝拉唑硫化物，而无需TBAB催化。全面的绿色化学指标分析表明，该方法比报道的雷贝拉唑硫化物更有效，更环保。
• 2-[(Phenylthio)methyl]pyridine derivatives: new antiinflammatory agents
  作者：Fortuna Haviv、Robert W. DeNet、Raymond J. Michaels、James D. Ratajczyk、George W. Carter、Patrick R. Young

  DOI：10.1021/jm00356a018

  日期：1983.2

  2-[(Phenylthio)methyl]pyridine derivatives inhibited the dermal reverse passive Arthus reaction (RPAR) in the rat. In the same model, indomethacin was inactive, and hydrocortisone was active. Compounds Ia-d also significantly reduced exudate volume and white blood cell accumulation in the pleural RPAR. This pattern of activity was similar to that of hydrocortisone and different from that of indomethacin

  2-[（（苯硫基）甲基]吡啶衍生物可抑制大鼠皮肤逆向被动Arthus反应（RPAR）。在同一模型中，消炎痛是无活性的，氢化可的松是有活性的。化合物Ia-d还显着减少了胸膜RPAR中的渗出液量和白细胞积聚。这种活性模式与氢化可的松相似，与消炎痛不同。
• Benzimidazoles, and their production formulation and use as gastric acid secretion inhibitors
  申请人：FISONS plc

  公开号：EP0174717A1

  公开（公告）日：1986-03-19

  There are described compounds of formula I, in which Rc is a nucleophilic nitrogen, oxygen or sulphur separated from the SO group by 1, 2, 3, 4 or 5 other atoms, R1, R1,R3 and R4, which may be the same or different, are each hydrogen, halogen, alkoxy, alkyl, fluoroalkyl, alkanoyl, RS(O)n-, -NO2, -N(R)2, -NHCOR, or -COOH or an ester or amide thereof, or an adjacent pair of R1, R2, R3 and R4 may in addition to the values given above, together form a chain -(CH2)x- or, together with the carbon atoms to which they are attached, form a 6 membered unsaturated carboxylic or nitrogen heterocyclic ring, x is 3, 4 or 5, n is 0, 1 or 2, X is 0, S or NR15, R15 is hydrogen, -COR, -COOR or alkyl which latter is optionally substituted by -OCOR, R is phenyl, or alkyl optionally substituted by phenyl, the phenyl groups in turn optionally being substituted by alkyl, provided that i) Rc is not -CH2CH2-morpholino, ii) that when Rc is a nitrogen nucleophile carried on an aryl or heteroaryl group R,5 is not a group -COR in which R is unsubstituted alkyl, iii) when X is NR15 Rc does not comprise an unsaturated nitrogen heterocyclic ring other than such a ring substituted by a either a) a substituted or unsubstituted amino group, or b) an N-oxido group, and iv) when X is NR15 Rc does not comprise an alkyl group substituted by an optionally alkyl or halo substitute piperidino group, and pharmaceutically acceptable salts thereof. There are also described processes for making the compounds, and their formulation and use as pharmaceuticals, e.g. to treat gastric acid secretion.

  所述化合物为式 I、 其中 Rc 是亲核的氮、氧或硫，与 SO 基团之间隔着 1、2、3、4 或 5 个原子、 R1、R1、R3 和 R4（可以相同或不同）各自为氢、卤素、烷氧基、烷基、氟烷基、烷酰基、RS(O)n-、-NO2、-N(R)2、-NHCOR 或 -COOH 或其酯或酰胺、 或相邻的一对 R1、R2、R3 和 R4 除上述数值外，还可共同形成链-(CH2)x-，或与它们所连接的碳原子一起形成一个 6 个成员的不饱和羧基或氮杂环、 x 是 3、4 或 5、 n 是 0、1 或 2、 X 是 0、S 或 NR15、 R15 是氢、-COR、-COR 或烷基，后者任选被-OCOR 取代、 R 是苯基，或任选被苯基取代的烷基，苯基又任选被烷基取代、 条件是 i) Rc 不是-CH2CH2-吗啉基，ii) 当 Rc 是芳基或杂芳基上携带的亲氮核物时，R,5 不是基团-COR，其中 R 是未取代的烷基、iii) 当 X 为 NR15 时，Rc 不包括不饱和氮杂环，但被 a）取代或未取代的氨基或 b）N-氧代基团取代的环除外；以及 iv) 当 X 为 NR15 时，Rc 不包括被任选烷基或卤代哌啶基取代的烷基、 及其药学上可接受的盐类。 此外，还描述了制造这些化合物的工艺，以及它们作为药物的配制和使用，例如用于治疗胃酸分泌。
• One-Pot Synthesis of 2-Benzyl/2-Allyl-Substituted Thiobenzoazoles Using Transition-Metal-Free Conditions in Water
  作者：Shi-Bo Zhang、Xing Liu、Ming-Yuan Gao、Zhi-Bing Dong

  DOI：10.1021/acs.joc.8b02136

  日期：2018.12.21

  A transition-metal-free protocol for the one-pot synthesis of 2-benzyl/2-allyl-substituted thiobenzoazoles in water was developed. The cyclization of 2-aminothiophenols, 2-aminophenols, and 1,2-phenylenediamines with tetramethylthiuram disulfide (TMTD) gave mercapto benzoheterocycles, and the subsequent C-S coupling with benzyl or allyl halides furnished the desired products in good to excellent yields. This method features transition-metal-free conditions with water as a solvent, an easy performance, mild reaction conditions, a wide substrate scope, and good to excellent yields, thus paving an efficient and useful way to establish a library of potentially active drug molecules.
• TOMIYAMA, TAKEHSI;TOMIYAMA, KAKU
  作者：TOMIYAMA, TAKEHSI、TOMIYAMA, KAKU

  DOI：——

  日期：——