4-methoxycarbonylmethanesulfonylbenzoic acid | 299181-79-6

• 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: 4-methoxycarbonylmethanesulfonylbenzoic acid
• 英文别名: 4-(2-Methoxy-2-oxoethyl)sulfonylbenzoic acid
• CAS: 299181-79-6
• 化学式: C₁₀H₁₀O₆S
• 分子量: 258.252
• InChiKey: DDXMHBZICFIWHI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  106
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-methoxycarbonylmethanesulfonylbenzoic acid 在 劳森试剂 、 ammonium hydroxide 、 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 生成 2-(4-thiocarbamoyl-benzenesulfonyl)acetic acid methyl ester
  参考文献：
  名称：

  Discovery of Small-Molecule Inhibitors of the ATPase Activity of Human Papillomavirus E1 Helicase

  摘要：

  The Boehringer Ingelheim compound collection was screened for inhibitors of the ATPase activity of human papillomavirus El helicase to develop antiviral agents that inhibit human papillomavirus (HPV) DNA replication. This screen led to the discovery of (biphenyl-4-sulfonyl)acetic acid 1, which inhibits the ATPase activity of HPV type 6 E1 helicase with a low micromolar IC50 value. A hit-to-lead exercise rapidly converted 1 into a low nanomolar lead series.

  DOI：

  10.1021/jm034206x
• 作为产物：
  描述：

  4-methoxycarbonylmethanesulfanylbenzoic acid 在 Oxone 作用下， 以 甲醇 、 水 为溶剂， 反应 16.0h， 以88%的产率得到4-methoxycarbonylmethanesulfonylbenzoic acid
  参考文献：
  名称：

  Discovery of Small-Molecule Inhibitors of the ATPase Activity of Human Papillomavirus E1 Helicase

  摘要：

  The Boehringer Ingelheim compound collection was screened for inhibitors of the ATPase activity of human papillomavirus El helicase to develop antiviral agents that inhibit human papillomavirus (HPV) DNA replication. This screen led to the discovery of (biphenyl-4-sulfonyl)acetic acid 1, which inhibits the ATPase activity of HPV type 6 E1 helicase with a low micromolar IC50 value. A hit-to-lead exercise rapidly converted 1 into a low nanomolar lead series.

  DOI：

  10.1021/jm034206x

文献信息

• [EN] ARYL SULFONIC ACIDS AND DERIVATIVES AS FSH ANTAGONISTS<br/>[FR] ACIDES SULFONIQUES ARYLES ET DERIVES TELS QUE LES ANTAGONISTES FSH
  申请人：AMERICAN HOME PROD

  公开号：WO2000058277A1

  公开（公告）日：2000-10-05

  This invention provides compounds of formula (I) having the structure wherein Q is hydrogen or -SO2R1; X is a bond, O, S(O)¿n?, -CH=CH-, -CH2CH2-, -C C-, or -CH2S(O)nCH2-; R?1¿ is OH, NH¿2?, C1 to C6 alkoxy, C1 to C3 perfluoroalkoxy; Ar is (a) or (b); Ar' is (c) or (d); R?2 and R4¿ are each, independently, hydrogen, OR6, -S(O)¿m?R?6, -NHR6, -N(R6)¿2, or -CH2SO2CH3; R?3 and R5¿ are each, independently, hydrogen, -NO¿2?, -NH2, -SO2R?9¿, or -CH¿2R?9; R6 is hydrogen, C¿1? to C6 alkyl, C3 to C6 alkenyl, -CH2CH2Z, -CH2COR?7, -CH¿2CH=CHCOR7, (e), (f) or (g); Y¿1? and Y?3¿ are each, independently, N, or CH; Y?2 and Y4¿ are each independently, O, S, or NR?13; R7 is -OR8, -NHR8, -N(R8)¿2, or -NHCH2CH2OR8; Z is -OR¿8?, -OCH2CH2OR?8, -N(R8)¿2, or (h); R8 is hydrogen or C1 to C3 alkyl; R9 is C1 to C6 alkyl, C3 to C6 alkenyl, OH, NHR?10, N(R10)¿2, CH2COR11, -CH2CH=CHCOR11, or (i); R10 is C1 to C3 alkyl, C3 to C4 alkenyl, phenyl, -CH2CH2OCH3, or -(j); R?11 is -OR12, -NHR12, -N(R12)¿2, or -NHCH2CH2OR12; R12 is hydrogen, or C¿1? to C3 alkyl; R?13¿ is hydrogen, or C¿1? to C3 alkyl; W is a bond, CH2, CH2CH2, O, S(O)q, NCHO, NCOCH3, or NR?12¿; m is 0 - 2; n is 0 - 2; q is 0 - 2, with the proviso that R?2 and R3¿ are not both hydrogen; or pharmaceutically acceptable salt thereof, which are useful as contraceptive agents.

  本发明提供了具有结构式(I)的化合物，其中Q为氢或-SO2R1; X为键，O，S(O)n，-CH=CH-，-CH2CH2-，-CC-或-CH2S(O)nCH2-; R1为OH，NH2，C1到C6烷氧基，C1到C3全氟烷氧基; Ar为(a)或(b); Ar'为(c)或(d); R2和R4分别独立地为氢，OR6，-S(O)mR6，-NHR6，-N(R6)2或-CH2SO2CH3; R3和R5独立地为氢，-NO2，-NH2，-SO2R9或-CH2R9; R6为氢，C1到C6烷基，C3到C6烯基，-CH2CH2Z，-CH2COR7，-CH2CH=CHCOR7，(e)，(f)或(g); Y1和Y3独立地为N或CH; Y2和Y4独立地为O，S或NR13; R7为-OR8，-NHR8，-N(R8)2或-NHCH2CH2OR8; Z为-OR8，-OCH2CH2OR8，-N(R8)2或(h); R8为氢或C1到C3烷基; R9为C1到C6烷基，C3到C6烯基，OH，NHR10，N(R10)2，CH2COR11，-CH2CH=CHCOR11或(i); R10为C1到C3烷基，C3到C4烯基，苯基，-CH2CH2OCH3或-(j); R11为-OR12，-NHR12，-N(R12)2或-NHCH2CH2OR12; R12为氢或C1到C3烷基; R13为氢或C1到C3烷基; W为键，CH2，CH2CH2，O，S(O)q，NCHO，NCOCH3或NR12; m为0-2; n为0-2; q为0-2，但R2和R3不能同时为氢; 或其药学上可接受的盐，其作为避孕剂有用。
• Aryl sulfonic acids and derivatives as FSH antagonists
  申请人：American Home Products Corporation

  公开号：US20020111369A1

  公开（公告）日：2002-08-15

  This invention provides compounds of formula I having the structure 1 wherein Q is hydrogen or —SO 2 R 1 ; X is a bond, O, S(O) n , —CH═CH—, —CH 2 CH 2 —, —C≡C—, or —CH 2 S(O) n CH 2 —; R 1 is OH, NH 2 , C 1 to C 6 alkoxy, C 1 to C 3 perfluoroalkoxy; 2 R 2 and R 4 are each, independently, hydrogen, OR 6 , —S(O) m R 6 , —NHR 6 , —N(R 6 ) 2 , or —CH 2 SO 2 CH 3 ; R 3 and R 5 are each, independently, hydrogen, —NO 2 , —NH 2 , —SO 2 R 9 , or —CH 2 R 9 ; R 6 is hydrogen, C 1 to C 6 alkyl, C 3 to C 6 alkenyl, —CH 2 CH 2 Z, —CH 2 COR 7 , —CH 2 CH═CHCOR 7 3 Y 1 and Y 3 are each, independently, N, or CH; Y 2 and Y 4 are each independently, O, S, or NR 13 ; R 7 is —OR 8 , —NHR 8 , —N(R 8 ) 2 , or —NHCH 2 CH 2 OR 8 ; Z is —OR 8 , —OCH 2 CH 2 OR 8 , —N(R 8 ) 2 , or 4 R 8 is hydrogen, or C 1 to C 3 alkyl; R 9 is C 1 to C 6 alkyl, C 3 to C 6 alkenyl, OH, NHR 10 , N(R 10 ) 2 , CH 2 COR 11 , —CH 2 CH═CHCOR 11 , or 5 R 10 is C 1 to C 3 alkyl, C 3 to C 4 alkenyl, phenyl, —CH 2 CH 2 OCH 3 , or 6 R 11 is —OR 12 , NHR 12 , —N(R 12 ) 2 , or —NHCH 2 CH 2 OR 12 ; R 12 is hydrogen, or C 1 to C 3 alkyl; R 13 is hydrogen, or C 1 to C 3 alkyl; W is a bond, CH 2 , CH 2 CH 2 , O, S(O) q , NCHO, NCOCH 3 , or NR 12 ; m is 0-2; n is 0-2; q is 0-2, with the proviso that R 2 and R 3 are not both hydrogen; or pharmaceutically acceptable salt thereof, which are useful as contraceptive agents.

  本发明提供了式I的化合物，其具有结构1， 其中， Q为氢或—SO2R1； X为键合，O，S(O)n，—CH═CH—，—CH2CH2—，—C≡C—或—CH2S(O)nCH2—； R1为OH，NH2，C1到C6烷氧基，C1到C3全氟烷氧基； R2和R4各自独立地为氢，OR6，—S(O)mR6，—NHR6，—N(R6)2或—CH2SO2CH3； R3和R5各自独立地为氢，—NO2，—NH2，—SO2R9或—CH2R9； R6为氢，C1到C6烷基，C3到C6烯基，—CH2CH2Z，—CH2COR7，—CH2CH═CHCOR73； Y1和Y3各自独立地为N或CH； Y2和Y4各自独立地为O，S或NR13； R7为—OR8，—NHR8，—N(R8)2或—NHCH2CH2OR8； Z为—OR8，—OCH2CH2OR8，—N(R8)2或 4 R8为氢或C1到C3烷基； R9为C1到C6烷基，C3到C6烯基，OH，NHR10，N(R10)2，CH2COR11，—CH2CH═CHCOR11或 5 R10为C1到C3烷基，C3到C4烯基，苯基，—CH2CH2OCH3或 6 R11为—OR12，NHR12，—N(R12)2或—NHCH2CH2OR12； R12为氢或C1到C3烷基； R13为氢或C1到C3烷基； W为键合，CH2，CH2CH2，O，S(O)q，NCHO，NCOCH3或NR12； m为0-2； n为0-2； q为0-2； 但R2和R3不能同时为氢； 或其药学上可接受的盐，其作为避孕剂具有用途。
• US6355633B1
  申请人：——

  公开号：US6355633B1

  公开（公告）日：2002-03-12
• US6437132B2
  申请人：——

  公开号：US6437132B2

  公开（公告）日：2002-08-20
• Discovery of Small-Molecule Inhibitors of the ATPase Activity of Human Papillomavirus E1 Helicase
  作者：Anne-Marie Faucher、Peter W. White、Christian Brochu、Chantal Grand-Maître、Jean Rancourt、Gulrez Fazal

  DOI：10.1021/jm034206x

  日期：2004.1.1

  The Boehringer Ingelheim compound collection was screened for inhibitors of the ATPase activity of human papillomavirus El helicase to develop antiviral agents that inhibit human papillomavirus (HPV) DNA replication. This screen led to the discovery of (biphenyl-4-sulfonyl)acetic acid 1, which inhibits the ATPase activity of HPV type 6 E1 helicase with a low micromolar IC50 value. A hit-to-lead exercise rapidly converted 1 into a low nanomolar lead series.