5-(benzo[d][1,3]dioxol-5-yl)thiophene-2-carboxylic acid | 1039859-57-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 5-(benzo[d][1,3]dioxol-5-yl)thiophene-2-carboxylic acid
• 英文别名: 5-(1,3-Benzodioxol-5-yl)thiophene-2-carboxylic acid
• CAS: 1039859-57-8
• 化学式: C₁₂H₈O₄S
• mdl: MFCD11189725
• 分子量: 248.259
• InChiKey: QQUOQIUCFSVSAR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.083
• 拓扑面积：
  84
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-(benzo[d][1,3]dioxol-5-yl)thiophene-2-carboxylic acid 、 二正丙胺 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以87%的产率得到5-(benzo[d][1,3]dioxol-5-yl)-N,N-dipropylthiophene-2-carboxamide
  参考文献：
  名称：

  Efficient Modulation of γ-Aminobutyric Acid Type A Receptors by Piperine Derivatives

  摘要：

  Piperine activates TRPV1 (transient receptor potential vanilloid type 1 receptor) receptors and modulates gamma-aminobutyric acid type A receptors (GABA(A)R). We have synthesized a library of 76 piperine analogues and analyzed their effects on GABA(A)R by means of a two-microelectrode voltage-clamp technique. GABA(A)R were expressed in Xenopus laevis oocytes. Structure-activity relationships (SARs) were established to identify structural elements essential for efficiency and potency. Efficiency of piperine derivatives was significantly increased by exchanging the piperidine moiety with either N,N-dipropyl, N,N-diisopropyl, N,N-dibutyl, p-methylpiperidine, or N,N-bis(trifluoroethyl) groups. Potency was enhanced by replacing the piperidine moiety by N,N-dibutyl, N,N-diisobutyl, or N,N-bistrifluoroethyl groups. Linker modifications did not substantially enhance the effect on GABA(A)R. Compound 23 [(2E,4E)-5-(1,3-benzodioxol-5-yl)-N,N-dipropyl-2,4-pentadienamide] induced the strongest modulation of GABA(A) (maximal GABA-induced chloride current modulation (IGABA-max = 1673% +/- 146%, EC50 = 51.7 +/- 9.5 mu M), while 25 [(2E,4E)-5-(1,3-benzodioxol-5-yl)-N,N-dibutyl-2,4-pentadienamide] displayed the highest potency (EC50 = 13.8 +/- 1.8 mu M, IGABA-max = 760% +/- 47%). Compound 23 induced significantly stronger anxiolysis in mice than piperine and thus may serve as a starting point for developing novel GABA(A)R modulators.

  DOI：

  10.1021/jm5002277
• 作为产物：
  描述：

  5-溴-2-羧基噻吩 、 3.4-(亚甲基二氧基)苯硼酸 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 以80 %的产率得到5-(benzo[d][1,3]dioxol-5-yl)thiophene-2-carboxylic acid
  参考文献：
  名称：

  胡椒酸衍生物作为分子调节剂，可加速 IAPP 聚集过程并改变其抗菌活性

  摘要：

  研究发现胡椒酸衍生物会影响胰岛淀粉样多肽 (IAPP) 的聚集过程。结构-活性关系研究表明，PAD-13是一种有效的分子调节剂，可通过促进初级和次级成核并降低其抗菌活性来加速 IAPP 原纤维的形成。

  DOI：

  10.1039/d3cc03363e

文献信息

• [EN] THIOPHENE -2- CARBOXYLIC ACID - (1H - BENZIMIDAZOL - 2 YL) - AMIDE DERIVATIVES AND RELATED COMPOUNDS AS INHIBITORS OF THE TEC KINASE ITK (INTERLEUKIN -2- INDUCIBLE T CELL KINASE) FOR THE TREATMENT OF INFLAMMATION, IMMUNOLOGICAL AND ALLERGIC DISORDERS<br/>[FR] DERIVES D'ACIDE THIOPHENE-2-CARBOXYLIQUE (1H-BENZIMIDAZOL-2 YL)-AMIDE ET COMPOSES ASSOCIES UTILISES COMME INHIBITEURS DE LA TEC KINASE ITK (KINASE DES LYMPHOCITES INDUCTIBLES PAR L'INTERLEUKINE -2) POUR TRAITER UNE INFLAMMATION ET DES TROUBLES IMMUNOLOGIQUES ET ALLERGIQUES
  申请人：BOEHRINGER INGELHEIM PHARMA

  公开号：WO2005079791A1

  公开（公告）日：2005-09-01

  Disclosed are compounds of formula (I): wherein Ar1, Ar2, R1, R2, R3, R4 and Xa are defined herein. The compounds of the invention inhibit Itk kinase and are therefore useful for treating diseases and pathological conditions involving inflammation, immunological disorders and allergic disorders. Also disclosed are processes for preparing these compounds and to pharmaceutical compositions comprising these compounds.

  揭示了式（I）的化合物：其中Ar1、Ar2、R1、R2、R3、R4和Xa在此定义。该发明的化合物抑制Itk激酶，因此对于治疗涉及炎症、免疫紊乱和过敏疾病的疾病和病理状况是有用的。还公开了制备这些化合物的方法以及包含这些化合物的药物组合物。
• Tec kinase inhibitors
  申请人：Bentzien Martin Joerg

  公开号：US20050209284A1

  公开（公告）日：2005-09-22

  Disclosed are compounds of formula(I): wherein Ar 1 , Ar 2 , R 1 , R 2 , R 3 , R 4 and X a are defined herein. The compounds of the invention inhibit Itk kinase and are therefore useful for treating diseases and pathological conditions involving inflammation, immunological disorders and allergic disorders. Also disclosed are processes for preparing these compounds and to pharmaceutical compositions comprising these compounds.

  本发明公开了式(I)的化合物：其中Ar1、Ar2、R1、R2、R3、R4和Xa的定义如下。本发明的化合物抑制Itk激酶，因此可用于治疗涉及炎症、免疫紊乱和过敏症的疾病和病理条件。本发明还公开了制备这些化合物的方法和包含这些化合物的药物组合物。
• NOVEL MCH RECEPTOR ANTAGONISTS
  申请人：Beck James Peter

  公开号：US20090170913A1

  公开（公告）日：2009-07-02

  The present invention relates to a melanin concentrating hormone antagonist compound of formula (I); wherein Ar 1 , L 1 , R 1 , q, X, R 2 , R 3 , R 4 , and R 5 are as defined, or a pharmaceutically acceptable salt, solvate, or enantiomer thereof useful in the treatment, prevention or amelioration of symptoms associated with obesity and related diseases.

  本发明涉及一种公式(I)的黑色素浓集激素拮抗剂化合物;其中Ar1，L1，R1，q，X，R2，R3，R4和R5如定义，或其药学上可接受的盐，溶剂合物或对映体，用于治疗，预防或改善与肥胖和相关疾病相关的症状。
• NOVEL CATECHOL DERIVATIVE AND PHARMACEUTICAL COMPOSITION COMPRISING SAME
  申请人：Autophagysciences, Inc

  公开号：EP3339299B1

  公开（公告）日：2021-03-03
• US7838543B2
  申请人：——

  公开号：US7838543B2

  公开（公告）日：2010-11-23