3-methoxy-N-(thien-2-ylmethyl)benzamide | 406679-32-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-methoxy-N-(thien-2-ylmethyl)benzamide
• 英文别名: 3-methoxy-N-thiophen-2-ylmethyl-benzamide；3-methoxy-N-(thiophen-2-ylmethyl)benzamide
• CAS: 406679-32-1
• 化学式: C₁₃H₁₃NO₂S
• 分子量: 247.318
• InChiKey: RCPZMRMSIOJNEK-UHFFFAOYSA-N

物化性质

• 沸点：
  430.5±35.0 °C(Predicted)
• 密度：
  1.212±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  66.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-methoxy-N-(thien-2-ylmethyl)benzamide 在 氯磺酸 、 三光气 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 9.0h， 生成 5-({[1-(3-methoxy-phenyl)methanoyl]-amino}-methyl)-thiophene-2-sulfonyl chloride
  参考文献：
  名称：

  Design, Synthesis, and Biological Activity of Novel, Potent, and Selective (Benzoylaminomethyl)thiophene Sulfonamide Inhibitors of c-Jun-N-Terminal Kinase

  摘要：

  Several lines of evidence support the hypothesis that c-Jun N-terminal kinases (JNKs) play a critical role in a wide range of disease states including cell death (apoptosis)-related and inflammatory disorders (epilepsy, brain, heart and renal ischemia, neurodegenerative diseases, multiple sclerosis, rheumatoid arthritis, and inflammatory bowel syndrome). The screening of a compound collection led to the identification of a 2-(benzoylaminomethyl)thiophene sulfonamide (AS004509, compound I) as a potent and selective JNK inhibitor. Chemistry and structure-activity relationship (SAR) studies performed around this novel kinase-inhibiting motif indicated that the left and central parts of the molecule were instrumental to maintaining potency at the enzyme. Accordingly, we investigated the JNK-inhibiting properties of a number of variants of the right-hand moiety of the molecule, which led to the identification of 2-(benzoylaminomethyl)thiophene sulfonamide benzotriazole (AS600292, compound 50a), the first potent and selective JNK inhibitor of this class which demonstrates a protective action against neuronal cell death induced by growth factor and serum deprivation.

  DOI：

  10.1021/jm031112e
• 作为产物：
  描述：

  2-噻吩甲胺 、 间甲氧基苯甲酰氯 在 吡啶 作用下， 以 氯仿 为溶剂， 反应 4.0h， 以99.9%的产率得到3-methoxy-N-(thien-2-ylmethyl)benzamide
  参考文献：
  名称：

  Pharmaceutically active sulfonamide derivatives bearing both lipophilic and ionisable moieties as inhibitors of protein Junkinases

  摘要：

  本发明涉及具有亲脂基团并在生理条件下基本可溶的磺胺基衍生物。所述化合物特别适用作药用活性化合物。本发明还涉及含有这种磺胺基衍生物的药物配方。所述磺胺基衍生物是JNK途径的高效调节剂，特别是JNK 2和3的高效和选择性抑制剂。本发明还涉及新型磺胺基衍生物以及它们的制备方法。 根据本发明的式I化合物适用于药用剂的那些化合物是这样的： Ar1和Ar2分别独立地是取代或未取代的芳基或杂环芳基， X是O或S，优选为O； R1是氢或C1-C6烷基，或R1与Ar1形成取代或未取代的5-6元饱和或不饱和环； n是0到5的整数，优选为1-3之间，最优选为1； 式I中的Y是未取代或取代的4-12元饱和环或双环烷基，其上取代有至少一个可离子化基团，该基团连接有一个亲脂链，并且含有至少一个氮原子，其中所述环中的一个氮原子与式I的磺酰基形成键合，从而提供磺胺基。

  公开号：

  EP1193268A1

文献信息

• [EN] PHENYL CARBOXAMIDE AND SULFONAMIDE DERIVATIVES FOR USE AS 11-BETA-HYDROXYSTEROID DEHYDROGENASE<br/>[FR] DERIVES DE CARBOXAMIDE DE PHENYLE ET DE SULFONAMIDE UTILISABLES COMME 11-BETA-HYDROXYSTEROIDE DESHYDROGENASE
  申请人：STERIX LTD

  公开号：WO2005042513A1

  公开（公告）日：2005-05-12

  There is provided a compound having Formula (I) R1-Z-R2 Formula (I) wherein R1 is an optionally substituted phenyl ring; R2 is or comprises an optionally substituted aromatic ring; and Z is -X-Y-L- or -Y-X-L- wherein either X is selected from -S(=O)(=O)- and -C(=O)-, and Y is -NR3-; or X is selected from -S(=O)(=O)- and -S-, and Y is -C(R4)(R5)-; L is an optional linker; and R3, R4 and R5 are each independently selected from H and hydrocarbyl; and wherein when R2 comprises the following structural moiety, Formula (II) wherein Q is an atom selected from the group consisting of S, O, N and C; the compound is selected from compounds of the formulae R1-C(=O)-NR3-L-R2; R1-S(=O)(=O)-C(R4)(R5)-L-R2; R1-S-C(R4)(R5)-L-R2; R1-NR3-S(=O)(=O)-L-R2; R1-NR3-C(=O)-L-R2; R1-C(R4)(R5)-S(=O)(=O)-L-R2; and R1-C(R4)(R5)-S-L-R2. These compounds are useful as 11β-hydroxysteriod dehydrogenase inhibitors in the treatment of i.a. diabetes.

  提供一种具有化学式（I）R1-Z-R2的化合物 其中R1是一个可选择取代的苯环; R2是或包括一个可选择取代的芳香环; Z是-X-Y-L-或-Y-X-L- 其中X被选自-S(=O)(=O)-和-C(=O)-，Y是-NR3-；或X被选自-S(=O)(=O)-和-S-，Y是-C(R4)(R5)-；L是可选的连接物；R3、R4和R5各自独立地选择自H和烃基；当R2包含以下结构基团时，该化合物被选择自以下化合物的化学式 R1-C(=O)-NR3-L-R2；R1-S(=O)(=O)-C(R4)(R5)-L-R2；R1-S-C(R4)(R5)-L-R2；R1-NR3-S(=O)(=O)-L-R2；R1-NR3-C(=O)-L-R2；R1-C(R4)(R5)-S(=O)(=O)-L-R2；和R1-C(R4)(R5)-S-L-R2。这些化合物在治疗糖尿病等疾病中作为11β-羟基类固醇脱氢酶抑制剂非常有用。
• Pharmaceutically active sulfonamide derivatives bearing both lipophilic and ionisable moietties as inhibitors of protein junkinases
  申请人：——

  公开号：US20040077854A1

  公开（公告）日：2004-04-22

  The present invention is related to sulfonamide derivatives having a lipophilic moiety and which are substantially soluble. Said compounds are notably for use as pharmaceutically active compounds. The present invention also related to pharmaceutical formulations containing such sulfonamide derivatives. Said sulfonamide derivatives are efficient modulators of the JNK pathway, they are in particular efficient and selective inhibitors of JNK 2 and 3. The present invention is furthermore related to novel sulfonamide derivatives as well as to methods of their preparation. The compounds of formula (I) according to the present invention being suitable pharmaceutical agents are those wherein Ar1 and Ar2 are independently from each other substituted or unsubstituted aryl or heteroaryl groups, X is O or S, preferably O;R1 is hydrogen or a C1-C6-alkyl group, or R1 forms a substituted or unsubstituted 5-6-membered saturated or unsaturated ring with Ar1;n is an integer from 0 to 5, preferably between 1-3 and most preferred 1;Y within formula (I) is an unsubstituted or a substituted 4-12-membered saturated cyclic or bicyclic alkyl which is substituted with at least one ionisable moiety to which a lipophilic chain is attached and which is containing at least one nitrogen atom, whereby one nitrogen atom within said ring is forming a bond with the sulfonyl group of formula (I) thus providing a sulfonamide.

  本发明涉及具有亲脂基团且基本溶解的磺酰胺衍生物，该化合物特别适用于作为药物活性化合物。本发明还涉及含有这种磺酰胺衍生物的药物制剂。该磺酰胺衍生物是JNK途径的有效调节剂，尤其是JNK2和3的有效和选择性抑制剂。本发明还涉及新的磺酰胺衍生物以及它们的制备方法。本发明所述的公式（I）化合物适用于药物制剂，其中Ar1和Ar2分别是取代或未取代的芳基或杂环芳基基团，X为O或S，优选为O；R1为氢或C1-C6烷基，或R1与Ar1形成取代或未取代的5-6元饱和或不饱和环；n为0到5的整数，优选为1-3，最优选为1；公式（I）中的Y是未取代或取代的4-12元饱和环或双环烷基，其被至少一个离子化基团取代，并连接有一个亲脂链，并且含有至少一个氮原子，其中该环中的一个氮原子与公式（I）中的磺酰基形成键合，从而提供磺酰胺。
• 11beta-hydroxysteroid dehydrogenase inhibitors
  申请人：Vicker Nigel

  公开号：US20050227987A1

  公开（公告）日：2005-10-13

  A compound having Formula I R 1 -Z-R 2 Formula I wherein R 1 is an optionally substituted phenyl ring; R 2 is or comprises an optionally substituted-aromatic ring; and Z is -X-Y-L- or -Y-X-L- wherein either X is selected from —S(═O)(═O)— and —C(═O)—, and Y is —NR 3 —; or X is selected from —S(═O)(═O)— and —S—, and Y is —C(R 4 )(R 5 )—; L is an optional linker; and R 3 , R 4 and R 5 are each independently selected from H and hydrocarbyl; and wherein when R 2 comprises the following structural moiety wherein Q is an atom selected from the group consisting of S, O, N and C; the compound is selected from compounds of the formulae R 1 C(═O)—NR 3 -L-R 2 ; R 1 —S(═O)(═O)—C(R 4 )(R 5 )-L-R 2 ; R 1 —S—C(R 4 )(R 5 )-L-R 2 ; R 1 —NR 3 —S(═O)(═O)-L-R 2 ; R 1 —NR 3 —C(═O)-L-R 2 ; R 1 —C(R 4 )(R 5 )—S(═O)(═O)-L-R 2 ; and R 1 —C(R 4 )(R 5 )—S-L-R 2 .

  化合物的化学式为IR1-Z-R2，其中R1为可选取代的苯环；R2为或包含可选取代的芳香环；Z为-X-Y-L-或-Y-X-L-，其中X选自—S(═O)(═O)—和—C(═O)—，Y为—NR3—；或X选自—S(═O)(═O)—和—S—，Y为—C(R4)(R5)—；L为可选的连接基；R3、R4和R5各自独立选择自H和烃基；当R2包含以下结构基团时Q为S、O、N和C中选择的原子，则该化合物被选择为下列化合物的公式：R1C(═O)—NR3-L-R2；R1—S(═O)(═O)—C(R4)(R5)-L-R2；R1—S—C(R4)(R5)-L-R2；R1—NR3—S(═O)(═O)-L-R2；R1—NR3—C(═O)-L-R2；R1—C(R4)(R5)—S(═O)(═O)-L-R2；和R1—C(R4)(R5)—S-L-R2。
• Pharmaceutically active sulfonamide derivatives bearing both lipophilic and ionisable moieties as inhibitors of Protein Jun-kinases
  申请人：Merck Serono SA

  公开号：EP1322642B1

  公开（公告）日：2013-09-04
• sHARMACEUTICALLY ACTIVE SULFONAMIDE DERIVATIVES BEARING BOTH LIPOPHILIC AND IONISABLE MOIETIES AS INHIBITORS OF PROTEIN JUNKINASES
  申请人：Applied Research Systems ARS Holding N.V.

  公开号：EP1322642A2

  公开（公告）日：2003-07-02