5-(4-(methylthio)phenyl)thiophene-2-carbaldehyde | 119307-04-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 5-(4-(methylthio)phenyl)thiophene-2-carbaldehyde
• 英文别名: 5-(4-methylthiophenyl)thienyl-2-carboxaldehyde；5-(4-methylsulfanylphenyl)thiophene-2-carbaldehyde
• CAS: 119307-04-9
• 化学式: C₁₂H₁₀OS₂
• 分子量: 234.343
• InChiKey: NGZULGHMZYAKRA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  70.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(4-(methylthio)phenyl)thiophene-2-carbaldehyde 生成 2-(2,2-dichloroethenyl)-5-(4-methylthiophenyl)thiophene
  参考文献：
  名称：

  BURKART, SUSAN E.;PHILLIPS, RICHARD B.;ROUSH, DAVID M.

  摘要：

  DOI：
• 作为产物：
  描述：

  5-溴噻吩-2-甲醛 在 四(三苯基膦)钯 、 溶剂黄146 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 0.5h， 生成 5-(4-(methylthio)phenyl)thiophene-2-carbaldehyde
  参考文献：
  名称：

  吡啶氮在钯催化亚胺水解中的作用：(E)-1-(3-溴噻吩-2-基)-N-(4-甲基吡啶-2-基)甲胺的案例研究

  摘要：

  在本研究中，4-甲基吡啶-2-胺与 3-溴噻吩-2-甲醛和席夫碱 (E)-1-(3-溴噻吩-2-基)-N-(4-甲基吡啶-2) 反应-基)甲胺以79%的产率获得。在 Suzuki 偶联反应条件下，使用 Pd(PPh3)4 作为催化剂，席夫碱与芳基/杂芳基硼酸的偶联，产生亚胺键（5a-5k，6a-6h）水解良好至中等的产物产量。为了深入了解过渡金属催化的化合物水解，进行了密度泛函理论 (DFT) 计算。理论计算有力地支持了实验，并提供了对过渡金属催化亚胺水解的深入了解。

  DOI：

  10.3390/molecules24142609
• 作为试剂：
  描述：

  5-溴噻吩-2-甲醛 、 4-甲硫基苯硼酸 在 5-(4-(methylthio)phenyl)thiophene-2-carbaldehyde 、 silica gel 、 EtOAc hexanes 作用下， 以5-(4-(Methylthio)phenyl)thiophene-2-carbaldehyde was obtained as a yellow solid (94%)的产率得到5-(4-(methylthio)phenyl)thiophene-2-carbaldehyde
  参考文献：
  名称：

  COMPOUNDS, PREPARATION AND USES THEREOF

  摘要：

  本发明提供了公式I的新化合物，包括这些化合物的制药组合物以及使用这些化合物作为抑制穿孔素活性的药剂或药物的方法，以及用于治疗处于风险或易感疾病或紊乱，或具有与不良穿孔素活性相关的疾病或紊乱的受试者。

  公开号：

  US20130065897A1

文献信息

• [EN] COMPOUNDS, PREPARATIONS AND USES THEREOF<br/>[FR] COMPOSÉS, LEURS PRÉPARATIONS ET LEURS UTILISATIONS
  申请人：PETER MACCALLUM CANCER INST

  公开号：WO2011075784A1

  公开（公告）日：2011-06-30

  The present invention provides novel compounds of the Formula (I), pharmaceutical compositions comprising such compounds and methods for using such compounds as agents or drugs for inhibiting perforin activity and for treating a subject at risk of or susceptible to a disease or disorder, or having a disease or disorder associated with undesirable perforin activity.

  本发明提供了式（I）的新化合物，包括这些化合物的药物组合物以及使用这些化合物作为抑制穿孔素活性的药剂或药物，用于治疗患有与不良穿孔素活性相关的疾病或紊乱、或处于患有风险或易感染某种疾病或紊乱的受试者的方法。
• 2-(2,2-dihaloethenyl)-5-arylthiophene pesticides
  申请人：FMC Corporation

  公开号：US04782079A1

  公开（公告）日：1988-11-01

  Thiophene derivatives of the following formula are effective as acaricides: ##STR1## wherein R.sub.A is selected from -hydrogen, -halogen, -lower alkyl, hydroxy, -lower alkoxy, -lower alkylthio, -lower alkoxyalkoxy, -lower alkoxycarbonyl, -aryloxycarbonyl, -lower alkoxycarbonyloxy, -lower alkylsulfonyl, -lower alkylsulfonyloxy, -arylsulfonyloxy, and -lower alkyl phosphonyloxy; R.sub.B is -hydrogen, or R.sub.A and R.sub.B together are --C.sub.4 H.sub.4 --bridging 2'-3' or 3'-4'; R.sub.3 and R.sub.4 are selected from -hydrogen, -lower alkyl, and -aryl; X is -halogen; and Y is selected from -hydrogen and -halogen.

  以下化学式的噻吩衍生物在杀螨剂中有效：其中 R.sub.A 从 -氢，-卤素，-较低烷基，羟基，-较低烷氧基，-较低烷基硫基，-较低烷氧基烷氧基，-较低烷氧基羰基，-芳基氧基羰基，-较低烷氧基羰氧基，-较低烷基磺酰基，-较低烷基磺酰氧基，-芳基磺酰氧基，和-较低烷基磷酰氧基中选择；R.sub.B 为-氢，或 R.sub.A 和 R.sub.B 一起为-二氢化-二氢噻吩-4-基-2-基-3-基或3-基-4-基；R.sub.3 和 R.sub.4 从 -氢，-较低烷基和-芳基中选择；X 为-卤素；Y 从-氢和-卤素中选择。
• [EN] INHIBITORS TARGETING DRUG-RESISTANT INFLUENZA A<br/>[FR] INHIBITEURS CIBLANT LA GRIPPE A PHARMACORÉSISTANTE
  申请人：UNIV PENNSYLVANIA

  公开号：WO2013086131A1

  公开（公告）日：2013-06-13

  Provided are compounds according to formula (la) or (lb) as described herein, that are capable of modulating the activity of influenza viruses (e.g., influenza A virus), for example, via interaction with the M2 transmembrane protein, and other similar viroporins. Also provided are methods for treating an influenza A-affected disease state or infection comprising administering a composition comprising one or more compounds according to according to formulas (la') or (lb), as described herein.

  根据本文描述的公式（la）或（lb），提供了一些化合物，这些化合物能够调节流感病毒（例如流感A病毒）的活性，例如通过与M2跨膜蛋白以及其他类似的病毒孔蛋白相互作用。还提供了一种治疗流感A感染疾病状态或感染的方法，包括通过给予包含根据本文描述的公式（la'）或（lb）的一个或多个化合物的组合物进行治疗。
• INHIBITORS TARGETING DRUG-RESISTANT INFLUENZA A
  申请人：THE TRUSTEES OF THE UNIVERSITY OF PENNSYLVANIA

  公开号：US20150191439A1

  公开（公告）日：2015-07-09

  Provided are compounds according to formula (Ia) or (Ib) as described herein, that are capable of modulating the activity of influenza viruses (e.g., influenza A virus), for example, via interaction with the M2 transmembrane protein, and other similar viroporins. Also provided are methods for treating an influenza A-affected disease state or infection comprising administering a composition comprising one or more compounds according to according to formulas (Ia′) or (Ib), as described herein.

  提供了符合公式（Ia）或（Ib）的化合物，可以通过与M2跨膜蛋白和其他类似的病毒孔蛋白相互作用，调节流感病毒（例如流感A病毒）的活性。还提供了一种治疗流感A受影响的疾病状态或感染的方法，包括给予含有一个或多个符合公式（Ia′）或（Ib）的化合物的组合物。
• Exploration of a Series of 5-Arylidene-2-thioxoimidazolidin-4-ones as Inhibitors of the Cytolytic Protein Perforin
  作者：Julie A. Spicer、Gersande Lena、Dani M. Lyons、Kristiina M. Huttunen、Christian K. Miller、Patrick D. O’Connor、Matthew Bull、Nuala Helsby、Stephen M. F. Jamieson、William A. Denny、Annette Ciccone、Kylie A. Browne、Jamie A. Lopez、Jesse Rudd-Schmidt、Ilia Voskoboinik、Joseph A. Trapani

  DOI：10.1021/jm401604x

  日期：2013.12.12

  A series of novel 5-arylidene-2-thioxoimidazolidin-4-ones were investigated as inhibitors of the lymphocyte-expressed pore-forming protein perform. Structure activity relationships were explored through variation of an isoindolinone or 3,4-dihydroisoquinolinone subunit on a fixed 2-thioxoimidazolidin-4-one/thiophene core. The ability of the resulting compounds to inhibit the lytic activity of both isolated perform protein and perforin delivered in situ by natural killer cells was determined. A number of compounds showed excellent activity at concentrations that were nontoxic to the killer cells, and several were a significant improvement on previous classes of inhibitors, being substantially more potent and soluble. Representative examples showed rapid and reversible binding to immobilized mouse perforin at low concentrations (<= 2.5 mu M) by surface plasmon resonance and prevented formation of perforin pores in target cells despite effective target cell engagement, as determined by calcium influx studies. Mouse PK studies of two analogues showed T-1/2 values of 1.1-1.2 h (dose of 5 mg/kg iv) and MTDs of 60-80 mg/kg (ip).