3-methyl-1-tosyl-1H-indole-6-carboxylic acid | 201286-75-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 3-methyl-1-tosyl-1H-indole-6-carboxylic acid
• 英文别名: 3-methyl-1-(4-toluenesulphonyl)-1 H-indole-6-carboxylic acid；3-Methyl-1-(4-methylphenyl)sulfonylindole-6-carboxylic acid
• CAS: 201286-75-1
• 化学式: C₁₇H₁₅NO₄S
• 分子量: 329.376
• InChiKey: MPYDVTVCMFTAQV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  84.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  在 二苯硒醚 、 tetrabutylammonium tetrafluoroborate 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 6.0h， 以87%的产率得到3-methyl-1-tosyl-1H-indole-6-carboxylic acid
  参考文献：
  名称：

  2-乙烯基苯胺的硒电催化环化对肽标记的吲哚

  摘要：

  可持续的硒电催化方法实现了 2-乙烯基苯胺的分子内环化，用于在极其温和的条件下合成具有肽标记的修饰吲哚

  DOI：

  10.1002/asia.202200762

文献信息

• Substituted azabicyclic compounds
  申请人：——

  公开号：US20020173527A1

  公开（公告）日：2002-11-21

  This invention is directed to physiologically active compounds of formula (I) 1 wherein 2 represents a bicyclic ring, system, of 9 ring members, in which the ring 3 is an oxazole, and the ring 4 is a benzene ring; R 1 represents hydrogen or a straight- or branched-chain alkyl group of 1 to about 4 carbon atoms, optionally substituted by hydroxy or one or more halogen atoms, or when Z 1 represents a direct bond R 1 may also represent a lower alkenyl or lower alkynyl group, or a formyl group; R 2 represents hydrogen, alkenyl, alkoxy, alkyl, alkylsulphinyl, alkylsulphonyl, alkylthio, aryl, arylalkyloxy, arylalkylsulphinyl, arylalkylsulphonyl, arylalkylthio, aryloxy, arylsulphinyl, arylsulphonyl, arylthio, cyano, cycloalkenyl, cycloalkenyloxy, cycloalkyl, cycloalkyloxy, hydroxy, —SO 2 NR 4 R 5 , —NR 4 SO 2 R 5 , —NR 4 R 5 , —C(═O)R 5 , —C(═O)C(═O)R 5 , —C(═O)NR 4 R 5 , —C(═O)OR 5 , —O(C═O)NR 4 R 5 , or —NR 4 C(═O)R 5 ; R 3 represents —C(═Z)—N(R 7 )R 6 ; A 1 represents a straight or branched C 1-6 alkylene chain optionally substituted by hydroxyl, alkoxy, oxo, cycloalkyl, aryl or heteroaryl; Z 1 represents a direct bond, an oxygen or sulphur atom or NH; n is zero; and mis 1; and N-oxides thereof, and their prodrugs, and pharmaceutically acceptable salts and solvates of the compounds of formula (I) and N-oxides thereof, and their prodrugs. Such compounds inhibit the production or physiological effects of TNF and inhibit cyclic AMP phosphodiesterase. The invention is also directed to pharmaceutical compositions comprising compounds of formula (I), their pharmaceutical use and methods for their preparation.

  本发明涉及公式（I）的生理活性化合物，其中2表示一个由9个环成的双环环系统，在该环3中为噁唑环，环4为苯环; R1表示氢或1至约4个碳原子的直链或支链烷基，可选地被羟基或一个或多个卤素原子取代，或当Z1表示直接键时，R1也可以表示低烯基或低炔基或甲酰基; R2表示氢、烯基、烷氧基、烷基、烷基磺酰基、烷基磺酰基、烷基硫基、芳基、芳基烷氧基、芳基烷基磺酰基、芳基烷基磺酰基、芳基烷基硫基、芳氧基、芳基磺酰基、芳基磺酰基、芳基硫基、氰基、环烯基、环烯基氧基、环烷基、环烷基氧基、羟基、-SO2NR4R5、-NR4SO2R5、-NR4R5、-C(═O)R5、-C(═O)C(═O)R5、-C(═O)NR4R5、-C(═O)OR5、-O(C═O)NR4R5或-NR4C(═O)R5; R3表示-C(═Z)-N(R7)R6; A1表示一条直链或支链C1-6烷基链，可选地被羟基、烷氧基、氧代、环烷基、芳基或杂环芳基取代; Z1表示直接键、氧原子或硫原子或NH; n为零; m为1;及其N-氧化物，以及公式（I）化合物和其N-氧化物的前药体，以及它们的制药可接受的盐和溶剂。这些化合物抑制TNF的产生或生理效应，并抑制环磷酸腺苷磷酸二酯酶。本发明还涉及包括公式（I）化合物的制药组合物，其制药用途和制备方法。
• 17BetaHSD Type 5 Inhibitor
  申请人：Niimi Tatsuya

  公开号：US20110071146A1

  公开（公告）日：2011-03-24

  To provide a novel and excellent method for treating and/or preventing prostatic cancer, benign prostatic hyperplasia, acne, seborrhea, hirsutism, baldness, alopecia, precocious puberty, adrenal hypertrophy, polycystic ovary syndrome, breast cancer, lung cancer, endometriosis, leiomyoma and the like based on selective inhibitory activity against 17βHSD type 5. It was found that an N-sulfonylindole derivative, where the indole ring is substituted by a carboxy group, a carboxy-substituted lower alkyl group or a carboxy-substituted lower alkenyl group at its carbon atom, has potent selective inhibitory activity against 17βHSD type 5 and may become a therapeutic agent and/or preventive agent for benign prostatic hyperplasia, prostatic cancer and the like without accompanying adverse drug reactions due to a decrease in testosterone, and the present invention has thus been completed.

  提供一种新颖和优秀的方法，用于基于对17βHSD类型5的选择性抑制活性，治疗和/或预防前列腺癌、良性前列腺增生、痤疮、脂溢性皮炎、多毛症、秃发、脱发、早熟、肾上腺增生、多囊卵巢综合症、乳腺癌、肺癌、子宫内膜异位症、平滑肌瘤等疾病。发现一种N-磺酰基吲哚衍生物，其中吲哚环在其碳原子上被羧基取代，或者被羧基取代的低烷基或低烯基取代，具有强大的选择性抑制17βHSD类型5的活性，可能成为治疗和/或预防良性前列腺增生、前列腺癌等疾病的治疗剂和/或预防剂，而不伴随着由于睾酮降低而产生的不良药物反应，因此本发明得以完成。
• 17BetaHSD TYPE 5 INHIBITOR
  申请人：Niimi Tatsuya

  公开号：US20090181960A1

  公开（公告）日：2009-07-16

  To provide a novel and excellent method for treating and/or preventing prostatic cancer, benign prostatic hyperplasia, acne, seborrhea, hirsutism, baldness, alopecia, precocious puberty, adrenal hypertrophy, polycystic ovary syndrome, breast cancer, lung cancer, endometriosis, leiomyoma and the like based on selective inhibitory activity against 17βHSD type 5. It was found that an N-sulfonylindole derivative, where the indole ring is substituted by a carboxy group, a carboxy-substituted lower alkyl group or a carboxy-substituted lower alkenyl group at its carbon atom, has potent selective inhibitory activity against 17βHSD type 5 and may become a therapeutic agent and/or preventive agent for benign prostatic hyperplasia, prostatic cancer and the like without accompanying adverse drug reactions due to a decrease in testosterone, and the present invention has thus been completed.

  提供一种新颖优良的方法，用于基于对17βHSD type 5的选择性抑制活性，治疗和/或预防前列腺癌、良性前列腺增生、痤疮、皮脂溢出、多毛症、脱发、早熟、肾上腺增生、多囊卵巢综合症、乳腺癌、肺癌、子宫内膜异位症、平滑肌瘤等疾病。发现一种N-磺酰基吲哚衍生物，其中吲哚环在其碳原子上被羧基、羧基取代的低碳基或羧基取代的低烯基取代，具有强大的选择性抑制17βHSD type 5的活性，可以成为治疗剂和/或预防剂，用于治疗良性前列腺增生、前列腺癌等疾病，不会伴随着由于睾酮减少而引起的不良药物反应，因此本发明已经完成。
• 17 BETA HSD TYPE 5 INHIBITOR
  申请人：Astellas Pharma Inc.

  公开号：EP1990335A1

  公开（公告）日：2008-11-12

  To provide a novel and excellent method for treating and/or preventing prostatic cancer, benign prostatic hyperplasia, acne, seborrhea, hirsutism, baldness, alopecia, precocious puberty, adrenal hypertrophy, polycystic ovary syndrome, breast cancer, lung cancer, endometriosis, leiomyoma and the like based on selective inhibitory activity against 17βHSD type 5. It was found that an N-sulfonylindole derivative, where the indole ring is substituted by a carboxy group, a carboxy-substituted lower alkyl group or a carboxy-substituted lower alkenyl group at its carbon atom, has potent selective inhibitory activity against 17βHSD type 5 and may become a therapeutic agent and/or preventive agent for benign prostatic hyperplasia, prostatic cancer and the like without accompanying adverse drug reactions due to a decrease in testosterone; and the present invention has thus been completed.

  提供一种基于对 17βHSD 5 型的选择性抑制活性的治疗和/或预防前列腺癌、良性前列腺增生、痤疮、脂溢性皮炎、多毛症、秃头、脱发、性早熟、肾上腺肥大、多囊卵巢综合征、乳腺癌、肺癌、子宫内膜异位症、子宫肌瘤等疾病的新型优良方法。 研究发现，一种 N-磺酰基吲哚衍生物，其吲哚环的碳原子上被羧基、羧基取代的低级烷基或羧基取代的低级烯基取代，对 17βHSD 5 型具有强效的选择性抑制活性，可成为良性前列腺增生、前列腺癌等的治疗剂和/或预防剂，且不会因睾酮减少而伴随药物不良反应；本发明由此完成。
• SUBSTITUTED AZABICYLIC COMPOUNDS AND THEIR USE AS INHIBITORS OF THE PRODUCTION OF TNF AND CYCLIC AMP PHOSPHODIESTERASE
  申请人：Aventis Pharma Limited

  公开号：EP0934307B1

  公开（公告）日：2011-04-27