(2-chloropyridin-3-yl)(thiophen-2-yl)methanol

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: (2-chloropyridin-3-yl)(thiophen-2-yl)methanol
• 英文别名: 2-Chloropyridin-3-yl-thiophen-2-yl-methanol；(2-chloropyridin-3-yl)-thiophen-2-ylmethanol
• 化学式: C₁₀H₈ClNOS
• 分子量: 225.699
• InChiKey: REKFSUXKEHKGTC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  61.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2-chloropyridin-3-yl)(thiophen-2-yl)methanol 在 copper(l) iodide 、 palladium 10% on activated carbon 、 potassium carbonate 、 三乙胺 、 三苯基膦 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 25.5h， 生成 ethyl 2-(3-((2-chloropyridin-3-yl)(thiophen-2-yl)methoxy)prop-1-ynyl)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate
  参考文献：
  名称：

  Synthesis and in vitro anti-proliferative effects of 3-(hetero)aryl substituted 3-[(prop-2-ynyloxy)(thiophen-2-yl)methyl]pyridine derivatives on various cancer cell lines

  摘要：

  A series of 3-(hetero) aryl substituted 3-[(prop-2-ynyloxy)(thiophen-2-yl)methyl]pyridine derivatives were designed as potential anticancer agents. These compounds were conveniently prepared by using Pd/C-Cu mediated Sonogashira type coupling as a key step. Many of these compounds were found to be promising when tested for their in vitro anti-proliferative properties against six cancer cell lines. All these compounds were found to be selective towards the growth inhibition of cancer cells with IC50 values in the range of 0.9-1.7 mu M (against MDA-MB 231 and MCF7 cells), comparable to the known anticancer drug doxorubicin. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.01.044
• 作为产物：
  描述：

  2-氯-3-(2-噻吩羰基)吡啶 在 potassium tert-butylate 、 C₃₇H₄₂Cl₂N₂OP₂Ru 、 叔丁醇 作用下， 以 二氯甲烷 、 异丙醇 为溶剂， 反应 3.0h， 以93%的产率得到(2-chloropyridin-3-yl)(thiophen-2-yl)methanol
  参考文献：
  名称：

  最小立体异构性Ru催化剂对重官能化二杂芳基和二芳基酮的不对称转移加氢

  摘要：

  使用具有最小立体感的Ru催化剂开发了高度官能化的二杂芳基和二芳基酮的高度对映选择性不对称转移氢化（ATH）。在结构上和电子上相似的基团连接在前手性中心上的各种酮底物都成功地还原成良好的至优异的对映选择性和产率。该方案可提供对手性二杂芳基甲醇和苯甲醇的实用而有效的途径，它们是药物和生物活性化合物的关键中间体。

  DOI：

  10.1021/acs.orglett.0c03064

文献信息

• Synthesis of 3-Arylthieno[2,3-b]-, -[2,3-c]- or -[3,2-c]pyridines Utilizing an Interrupted Pummerer Reaction
  作者：Kazuhiro Kobayashi、Teruhiko Suzuki、Mai Horiuchi、Yasuhiko Shiroyama、Hisatoshi Konishi

  DOI：10.1055/s-0030-1260152

  日期：2011.9

  yl)pyridines, 4-(1-arylethenyl)-3-(ethylsulfinyl)pyridines, and 3-(1-arylethenyl)-4-(ethylsulfinyl)pyridines, which can be easily prepared from the respective aryl chloropyridinyl ketones in a three-step sequence, undergo an interrupted Pummerer reaction on treatment with excess acetic anhydride at temperatures ranging from 100 to 130 ˚C to give 3-arylthieno[2,3-b]pyridines, 3-aryl­thieno[2,3-c]pyridines

  已经开发了合成三种类型的噻吩并吡啶的有效方法。因此，3-（1-芳基乙烯基）-2-（乙基亚磺酰基）吡啶，4-（1-芳基乙烯基）-3-（乙基亚磺酰基）吡啶和3-（1-芳基乙烯基）-4-（乙基亚磺酰基）吡啶可可以容易地由三步顺序的各个芳基氯吡啶基酮制备，在过量的乙酸酐中于100至130°C的温度下进行间歇Pummerer反应，得​​到3-芳基噻吩并[2,3- b ]吡啶， 3-芳基噻吩并[3，2- c ]吡啶和3-芳基噻吩并[3，2- c ]吡啶。 噻吩并[2,3- b ]吡啶-噻吩并[2,3- c ]吡啶-噻吩并[3,2- c ]吡啶-Pummerer反应中断-乙酸酐
• Pyrido[2,3-D]pyrimidine derivatives and pharmaceutical compositions
  申请人：Yamanouchi Pharmaceutical Co., Ltd.

  公开号：US06136810A1

  公开（公告）日：2000-10-24

  This invention relates to compounds (I) or pharmaceutically acceptable salts thereof, having a function to inhibit type IV phosphodiesterase (PDE) ##STR1## [X: an oxygen atom or a sulfur atom, R.sup.1 : a lower alkyl group, a cycloalkyl-lower alkyl group or a cycloalkyl group, R.sup.2 : a hydrogen atom, a halogen atom, a lower alkyl group, a halogeno-lower alkyl group, a hydroxy-lower alkyl group, a mercapto-lower alkyl group, a lower alkoxy-lower alkyl group, a lower alkylthio-lower alkyl group, a lower alkanoyloxy-lower alkyl group, a lower alkanoylthio-lower alkyl group, a lower alkanoyl-lower alkyl group, a hydroxyimino-lower alkyl group, a lower alkoxyimino-lower alkyl group, a cycloalkyl group, an aryl group or a lower alkanoyl group, R.sup.3 : a hydrogen atom, a halogen atom or a lower alkyl group, R.sup.4 : a hydrogen atom or a lower alkyl group, R.sup.5 : a cycloalkyl group; a naphthyl group substituted; a five- or six-membered monocyclic hetero ring group having 1 to 4 hetero atoms selected from nitrogen atom, oxygen atom and sulfur atom; or a group represented by the formula ##STR2## amd F.sup.6 : a halogen atom, a lower alkyl group, a halogeno-lower alkyl group, a hydroxyl group, a lower alkoxy group, a cyano group or a nitro group].

  这项发明涉及化合物（I）或其药学上可接受的盐，具有抑制第IV型磷酸二酯酶（PDE）的功能。
• PYRIDO [2,3-D] PYRIMIDINE DERIVATIVES AND MEDICINAL COMPOSITIONS THEREOF
  申请人：YAMANOUCHI PHARMACEUTICAL CO., LTD.

  公开号：EP0885894A1

  公开（公告）日：1998-12-23

  Compounds represented by general formula (I) or pharmaceutically acceptable salts thereof which have the effect of inhibiting the activity of type IV phosphodiesterases and are usable as drugs, in particular, type IV phosphodiesterase inhibitors or preventives and remedies for diseases in association with the sthenic type IV phosphodiesterase activity, in particular, respiratory diseases such as bronchial asthma. In said formula (I), X represents oxygen or sulfur; R1 represents lower alkyl, cycloalkyl(lower alkyl) or cycloalkyl; R2 represents hydrogen, halogeno, lower alkyl, halo(lower alkyl), hydroxy(lower alkyl), mercapto(lower alkyl), (lower alkoxy)(lower alkyl), (lower alkylthio)(lower alkyl), (lower alkanoyloxy)(lower alkyl), (lower alkanoylthio)(lower alkyl), (lower alkanoyl)(lower alkyl), hydroxyimino(lower alkyl), (lower alkoxyimino)(lower alkyl), cycloalkyl, aryl or lower alkanoyl; R3 represents hydrogen, halogeno or lower alkyl; R4 represents hydrogen, or lower alkyl; R5 represents cycloalkyl optionally substituted by the same group as R6; naphthyl optionally substituted by the same group as R6 a 5- or 6-membered monocyclic heterocycle optionally substituted by the same group as R6, optionally fused with a benzene ring and having one to four heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur atoms; or a group of formula (a); and R6 represents halogeno, lower alkyl, halo(lower alkyl), hydroxy, lower alkoxy, cyano or nitro.

  由通式(I)代表的化合物或其药学上可接受的盐，具有抑制IV型磷酸二酯酶活性的作用，可用作药物，特别是IV型磷酸二酯酶抑制剂或预防和治疗与sthenic IV型磷酸二酯酶活性有关的疾病，特别是呼吸系统疾病，如支气管哮喘。在所述式（I）中，X 代表氧或硫；R1 代表低级烷基、环烷基（低级烷基）或环烷基；R2 代表氢、卤素、低级烷基、卤代（低级烷基）、羟基（低级烷基）、巯基（低级烷基）、（低级烷氧基）（低级烷基）、（低级烷硫基）（低级烷基）、（低级烷酰氧基）（低级烷基）、（低级烷酰硫基）（低级烷基）、（低级烷酰基）（低级烷基）、羟基亚氨基（低级烷基）、（低级烷氧基亚氨基）（低级烷基）、环烷基、芳基或低级烷酰基；R3 代表氢、卤素或低级烷基；R4 代表氢或低级烷基；R5 代表环烷基，可任选被与 R6 相同的基团取代；萘基，可任选被与 R6 相同的基团取代；5 或 6 元单环杂环，可任选被与 R6 相同的基团取代，可任选与苯环融合，并具有一至四个杂原子，这些杂原子选自由氮、氧和硫原子组成的组；或式 (a) 的基团；以及 R6 代表卤素、低级烷基、卤代（低级烷基）、羟基、低级烷氧基、氰基或硝基。
• Synthesis of indole based novel small molecules and their in vitro anti-proliferative effects on various cancer cell lines
  作者：Balakrishna Dulla、E. Sailaja、Upendar Reddy CH、Madhu Aeluri、Arunasree M. Kalle、S. Bhavani、D. Rambabu、M.V. Basaveswara Rao、Manojit Pal

  DOI：10.1016/j.tetlet.2013.12.050

  日期：2014.1

  Indole based novel small molecules were designed as potential anticancer agents. Multi step synthesis of these compounds was carried out by using Pd/C-Cu mediated coupling-cyclization strategy as a key step. The single crystal X-ray diffraction study was used to confirm the molecular structure of a representative compound unambiguously. Many of these compounds were evaluated for their anti-proliferative properties in vitro against six cancer cell lines as well as noncancerous cells. All these compounds showed selective growth inhibition of cancer cells and several of them were found to be promising with IC50 values in the range of 0.1-1.2 mu M, comparable to the known anticancer drug doxorubicin. (C) 2013 Elsevier Ltd. All rights reserved.
• US6136810A
  申请人：——

  公开号：US6136810A

  公开（公告）日：2000-10-24