5'-溴螺[环戊烷-1,3'-吲哚]-2'-酮 | 304876-16-2

• 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
• 中文名称: 5'-溴螺[环戊烷-1,3'-吲哚]-2'-酮
• 英文名称: 5-bromospiro[cyclopentane-1,3'-[3H]indol]-2'(1'H)-one
• 英文别名: 5'-bromospiro[cyclopentane-1,3'-indolin]-2'-one；5'-bromo-1'H-spiro[cyclopentane-1,3'-indol]-2'-one；5-bromospiro[cyclopentane-1,3-indoline]-2-one；5'-bromospiro[cyclopentane-1,3'-indol]-2'(1'H)-one；5-bromospiro[1H-indole-3,1'-cyclopentane]-2-one
• CAS: 304876-16-2
• 化学式: C₁₂H₁₂BrNO
• mdl: MFCD13192266
• 分子量: 266.137
• InChiKey: DSJAYULUMZHCII-UHFFFAOYSA-N

物化性质

• 沸点：
  415.8±45.0 °C(Predicted)
• 密度：
  1.57±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.416
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  5'-溴螺[环戊烷-1,3'-吲哚]-2'-酮 在 三乙基硅烷 、 正丁基锂 、 三氟化硼乙醚 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 22.5h， 生成 5-[(2,6-dimethyl-4-triisopropylsilyloxyphenyl)methyl]spiro[cyclopentane-1,3-indoline]-2-one
  参考文献：
  名称：

  一种作为甲状腺激素β受体激动剂的化合物及其用途

  摘要：

  本发明涉及一种作为甲状腺激素β受体激动剂的化合物及其用途，进一步涉及包含所述化合物的药物组合物。本发明所述的化合物或药物组合物可以制备用于预防、治疗或减轻由甲状腺激素β受体激动剂调节的药物，尤其用于制备治疗非酒精性脂肪性肝病的药物。

  公开号：

  CN112300211A
• 作为产物：
  描述：

  2-吲哚酮 在 正丁基锂 、 四甲基乙二胺 、 溴 、 sodium acetate 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 生成 5'-溴螺[环戊烷-1,3'-吲哚]-2'-酮
  参考文献：
  名称：

  New progesterone receptor antagonists: 3,3-disubstituted-5-aryloxindoles

  摘要：

  A neck series of 3,3-disubstituted-5-aryloxindoles has been synthesized and evaluated for progesterone receptor antagonist (PR) activity in a T47D cell alkaline phosphatase assay and for their ability to bind PR in competition binding studies. In this communication, the synthesis and structurc-activiy relationships (SARs) of various 3,3-substituents are discussed where it is clear that small alkyl and spiroalkyl groups are required to achieve better PR antagonist activity. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00746-1

文献信息

• Thio-oxindole derivatives
  申请人：American Home Products Corporation

  公开号：US06355648B1

  公开（公告）日：2002-03-12

  This invention relates to compounds which are agonists of the progesterone receptor which have the general structures: wherein: R1 and R2 are H, alkyl, substituted alkyl; OH; O(alkyl); O(substituted alkyl); OAc; aryl; substituted aryl; heteroaryl; substituted heteroaryl; alkylaryl; alkylheteroaryl; 1-propynyl; or 3-propynyl; or R1 and R2 are joined to form an alkyl, alkenyl or heterocyclic ring; or R1 and R2 together comprise a double bond to CMe2; C(cycloalkyl), O, or C(cycloether); R3 is H, OH, NH2, C1 to C6 alkyl, substituted C1 to C6 alkyl, C3 to C6 alkenyl, alkynyl, substituted alkynyl, or CORA; RA is H, C1 to C3 alkyl, substituted C1 to C3 alkyl, C1 to C3 alkoxy, substituted C1 to C3 alkoxy, C1 to C3 aminoalkyl, or substituted C1 to C3 aminoalkyl; R4 is H, halogen, CN, NH2, NO2, C1 to C6 alkyl, or substituted C1 to C6 alkyl, C1 to C6 alkoxy, substituted C1 to C6 alkoxy, C1 to C6 aminoalkyl, or substituted C1 to C6 aminoalkyl; R5 is optionally substituted and selected from a benzene ring, a five or six membered heterocyclic ring with 1, 2, or 3 heteroatoms selected from O, S, SO, SO2 or NR6; or an indol-4-yl, indol-7-yl or benzo-2-thiophene moiety; Q1 is S, NR7, CR8R9; or a pharmaceutically acceptable salt thereof, as well as methods of using these compounds to induce contraception or treat progesterone-related carcinomas and adenocarcinomas.

  这项发明涉及激素受体的激动剂化合物，其具有以下一般结构： 其中： R1和R2为H、烷基、取代烷基；OH；O(烷基)；O(取代烷基)；OAc；芳基；取代芳基；杂环芳基；取代杂环芳基；烷基芳基；烷基杂环芳基；1-丙炔基；或3-丙炔基；或R1和R2连接形成烷基、烯基或杂环环；或R1和R2共同包括与CMe2形成双键的C(环烷基)、O或C(环醚)；R3为H、OH、NH2、C1至C6烷基、取代C1至C6烷基、C3至C6烯基、炔基、取代炔基，或CORA；RA为H、C1至C3烷基、取代C1至C3烷基、C1至C3烷氧基、取代C1至C3烷氧基、C1至C3氨基烷基，或取代C1至C3氨基烷基；R4为H、卤素、CN、NH2、NO2、C1至C6烷基，或取代C1至C6烷基、C1至C6烷氧基，取代C1至C6烷氧基、C1至C6氨基烷基，或取代C1至C6氨基烷基；R5为可选择取代并选自苯环、具有1、2或3个来自O、S、SO、SO2或NR6的杂原子的五元或六元杂环环；或吲哚-4-基、吲哚-7-基或苯并-2-噻吩基团；Q1为S、NR7、CR8R9；或其药学上可接受的盐，以及使用这些化合物诱导避孕或治疗与孕激素相关的癌症和腺癌的方法。
• Cyanopyrroles
  申请人：American Home Products Corporation

  公开号：US20020068735A1

  公开（公告）日：2002-06-06

  This invention provides a progesterone receptor antagonist of formula 1 having the structure 1 wherein T is O, S, or absent; R 1 , and R 2 are each, independently, hydrogen, alkyl, substituted alkyl; or R 1 and R 2 are taken together form a ring and together contain —CH 2 (CH 2 ) n CH 2 —, —CH 2 CH 2 CMe 2 CH 2 CH 2 —, —O(CH 2 ) p CH 2 —, —O(CH 2 ) q O—, —CH 2 CH 2 OCH 2 CH 2 —, or —CH 2 CH 2 NR 7 CH 2 CH 2 —; n=1-5; p=1-4; q=1-4; R 3 is hydrogen, OH, NH 2 , alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, or COR A ; R A is hydrogen, alkyl, substituted alkyl, alkoxy, substituted alkoxy, aminoalkyl, or substituted aminoalkyl; R 4 is hydrogen, halogen, CN, NH 2 , alkyl, substituted alkyl, alkoxy, substituted alkoxy, aminoalkyl, or substituted aminoalkyl; R 5 is hydrogen, alkyl, or substituted alkyl; R 6 is hydrogen, alkyl, substituted alkyl, or COR B , R B is hydrogen, alkyl, substituted alkyl, alkoxy, substituted alkoxy, aminoalkyl, or substituted aminoalkyl; R 7 is hydrogen or alkyl; or a pharmaceutically acceptable salt thereof

  这项发明提供了一种具有结构的孕酮受体拮抗剂 1 其中T为O、S或不存在；R 1 和R 2 分别为氢、烷基、取代烷基；或R 1 和R 2 一起形成一个环，并且一起含有—CH 2 (CH 2 ) n CH 2 —、—CH 2 CH 2 CMe 2 CH 2 CH 2 —、—O(CH 2 ) p CH 2 —、—O(CH 2 ) q O—、—CH 2 CH 2 OCH 2 CH 2 —或—CH 2 CH 2 NR 7 CH 2 CH 2 —； n=1-5；p=1-4；q=1-4； R 3 为氢、OH、NH 2 、烷基、取代烷基、烯基、取代烯基、炔基、取代炔基或COR A ； R A 为氢、烷基、取代烷基、烷氧基、取代烷氧基、氨基烷基或取代氨基烷基； R 4 为氢、卤素、CN、NH 2 、烷基、取代烷基、烷氧基、取代烷氧基、氨基烷基或取代氨基烷基； R 5 为氢、烷基或取代烷基； R 6 为氢、烷基、取代烷基或COR B ， R B 为氢、烷基、取代烷基、烷氧基、取代烷氧基、氨基烷基或取代氨基烷基； R 7 为氢或烷基；或其药学上可接受的盐
• CHEMOSELECTIVE METHYLENE HYDROXYLATION IN AROMATIC MOLECULES
  申请人：The Board of Trustees of the University of Illinois

  公开号：US20200087331A1

  公开（公告）日：2020-03-19

  A chemoselective and reactive Mn(CF 3 -PDP) catalyst system that enables for the first time the strategic advantages of late-stage aliphatic C—H hydroxylation to be leveraged in aromatic compounds. This discovery will benefit small molecule therapeutics by enabling the rapid diversification of aromatic drugs and natural products and identification of their metabolites.

  一种化学选择性和反应性的Mn(CF3-PDP)催化体系首次实现了后期脂肪族C—H羟基化在芳香化合物中的战略优势。这一发现将有助于小分子药物的快速多样化和芳香类药物以及天然产物的代谢产物的鉴定。
• Design, Synthesis, and SAR of New Pyrrole-Oxindole Progesterone Receptor Modulators Leading to 5-(7-Fluoro-3,3-dimethyl-2-oxo-2,3-dihydro-1<i>H</i>-indol-5-yl)-1-methyl-1<i>H</i>-pyrrole-2-carbonitrile (WAY-255348)
  作者：Andrew Fensome、William R. Adams、Andrea L. Adams、Tom J. Berrodin、Jeff Cohen、Christine Huselton、Arthur Illenberger、Jeffrey C. Kern、Valerie A. Hudak、Michael A. Marella、Edward G. Melenski、Casey C. McComas、Cheryl A. Mugford、Ov D. Slayden、Matthew Yudt、Zhiming Zhang、Puwen Zhang、Yuan Zhu、Richard C. Winneker、Jay E. Wrobel

  DOI：10.1021/jm701080t

  日期：2008.3.1

  We have continued to explore the 3,3-dialkyl-5-aryloxindole series of progesterone receptor (PR) modulators looking for new agents to be used in female healthcare: contraception, fibroids, endometriosis, and certain breast cancers. Previously we reported that subtle structural changes with this and related templates produced functional switches between agonist and antagonist properties ( Fensome et

  我们继续探索3,3-二烷基-5-芳基吲哚系列孕酮受体（PR）调节剂，以寻找用于女性保健的新药物：避孕，肌瘤，子宫内膜异位症和某些乳腺癌。先前，我们报道了该模板和相关模板的微妙结构变化在激动剂和拮抗剂特性之间产生了功能转换（Fensome等，Biorg。Med。Chem。Lett。2002，12，3487; 2003，13，1317）。我们在本文中报道了5-（2-氧代吲哚-5-基）-1 H-吡咯-2-腈类化合物中的新功能开关。我们发现3，3-二烷基取代基的大小对于控制功能响应很重要。因此，小的基团（二甲基）提供有效的PR拮抗剂，而较大的基团（螺环己基）是PR激动剂。
• Cyclic regimens utilizing indoline derivatives
  申请人：WYETH

  公开号：US20030050288A1

  公开（公告）日：2003-03-13

  This invention relates to cyclic combination therapies and regimens utilizing substituted indoline derivative compounds which are antagonists of the progesterone receptor having the general structure: 1 wherein R 1 and R 2 may be single substituents or fused to form spirocyclic rings, in combination with progestins, estrogens, or both. These methods of treatment may be used for contraception, for the treatment and/or prevention of secondary amenorrhea, dysfunctional bleeding, uterine leiomyomata, endometriosis, polycystic ovary syndrome, carcinomas and adenocarcinomas of the endometrium, ovary, breast, colon, or prostate, minimization of side effects, cyclic menstrual bleeding, or stimulation of food intake.

  本发明涉及使用取代的吲哚啉衍生物化合物作为孕激素受体拮抗剂，其具有以下一般结构式：1其中R1和R2可以是单个取代基或融合形成螺环，并与孕激素、雌激素或两者结合使用的循环组合疗法和方案。这些治疗方法可用于避孕、治疗和/或预防继发性闭经、功能性出血、子宫平滑肌瘤、子宫内膜异位症、多囊卵巢综合症、子宫内膜、卵巢、乳腺、结肠或前列腺的癌症和腺癌、减少副作用、循环月经出血或刺激食欲。