2-iodo-4-(methylsulfonyl)phenylamine | 251548-94-4

• 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: 2-iodo-4-(methylsulfonyl)phenylamine
• 英文别名: 2-iodo-4-(methanesulfonyl)aniline；2-iodo-4-(methylsulfonyl)aniline；2-iodo-4-(methanesulfonyl)phenylamine；2-iodo-4-methanesulfonyl-phenylamine；2-iodo-methanesulfonylaniline；2-iodo-4-methylsulfonylaniline
• CAS: 251548-94-4
• 化学式: C₇H₈INO₂S
• 分子量: 297.117
• InChiKey: QEFGKGMHWLOVLS-UHFFFAOYSA-N

物化性质

• 熔点：
  201-202 °C
• 沸点：
  438.9±45.0 °C(Predicted)
• 密度：
  1.909±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  68.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-iodo-4-(methylsulfonyl)phenylamine 在 palladium diacetate 、 硅酸四乙酯 、 4-甲基苯磺酸吡啶 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 ethyl [7-(methylsulfonyl)-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl]acetate
  参考文献：
  名称：

  Discovery of a Potent and Selective Prostaglandin D₂ Receptor Antagonist, [(3R)-4-(4-Chloro- benzyl)-7-fluoro-5-(methylsulfonyl)-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl]-acetic Acid (MK-0524)

  摘要：

  The discovery of the potent and selective prostaglandin D-2 (PGD(2)) receptor (DP) antagonist [(3R)-4-(4-chlorobenzyl)-7-fluoro-5-(methylsulfonyl)-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl]-acetic acid (13)is presented. Initial lead antagonists 6and 7were found to be potent and selective DP antagonists (DP K-i = 2.0 nM for each); however, they both suffered from poor pharmacokinetic profiles, short half-lives and high clearance rates in rats. Rat bile duct cannulation studies revealed that high concentrations of parent drug were present in the biliary fluid (C-max = 1100 mu M for 6and 3900 mu M for 7). This pharmacokinetic liability was circumvented by replacing the 7-methylsulfone substituent present in 6and 7with a fluorine atom resulting in antagonists with diminished propensity for biliary excretion and with superior pharmacokinetic profiles. Further optimization led to the discovery of the potent and selective DP antagonist 13.

  DOI：

  10.1021/jm0603668
• 作为产物：
  描述：

  2,2-dimethyl-N-(2-iodo-4-methanesulfonylphenyl)propionamide 在 氢氧化钾 、 水 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 2-iodo-4-(methylsulfonyl)phenylamine
  参考文献：
  名称：

  Heterocyclic indole derivatives and mono- or diazaindole derivatives

  摘要：

  提供一种化合物，其一般式表示为（1）：其中Het代表可选择地取代的杂环基团；A1和A2各自独立地表示—CH═等；A3表示—CH2—等；R1表示4-氟苯基团等；R2表示烷基团；n表示0、1或2，但当A1和A2都为—CH═时，A3表示—CH2—或—SO2—，它是一种COX-2抑制活性的吲哟衍生物或单或二氮杂吲哟衍生物，可用作药物，如抗炎药物，或其与药用可接受的酸或碱形成的加合盐，或其水合物。

  公开号：

  US06673797B1

文献信息

• Aromatic amides
  申请人：Eli Lilly and Company

  公开号：US06635657B1

  公开（公告）日：2003-10-21

  This application relates to a compound of formula I (or a pharmaceutically acceptable salt thereof) as defined herein, pharmaceutical compositions thereof, and its use as an inhibitor of factor Xa, as well as a process for its preparation and intermediates therefor.

  本申请涉及式I化合物（或其药用可接受的盐），如本文所述，其药物组合物，及其作为因子Xa抑制剂的用途，以及其制备过程和中间体。
• Pyrroloquinoline Derivatives And Their Use As Protein Kinases Inhibitors
  申请人：Bienayme Hugues

  公开号：US20090042876A1

  公开（公告）日：2009-02-12

  The present invention relates to inhibitors of protein kinases of formula I: which can be used in the treatment of various diseases, notably cancer, inflammation or disorders of the central nervous system. It also relates to pharmaceutical compositions containing the compounds according to the invention and their use in therapy.

  本发明涉及式I的蛋白激酶抑制剂，可用于治疗各种疾病，特别是癌症、炎症或中枢神经系统疾病。还涉及含有根据本发明的化合物的药物组合物及其在治疗中的应用。
• [EN] INDOLYLMETHYL-MORPHOLINE DERIVATIVES AS KINASE INHIBITORS<br/>[FR] DERIVES D'INDOLYLMETHYL-MORPHOLINE EN TANT QU'INHIBITEURS DES KINASES
  申请人：UCB PHARMA SA

  公开号：WO2010146351A1

  公开（公告）日：2010-12-23

  A series of morpholine derivatives, substituted in the 4-position by a substituted carbonyl or sulfonyl moiety, and in the 3-position by an optionally substituted indol-3-ylmethyl group, being selective inhibitors of PI3 kinase enzymes, are accordingly of benefit in medicine, for example in the treatment of inflammatory, autoimmune, cardiovascular, neurodegenerative, metabolic, oncological, nociceptive or ophthalmic conditions.

  一系列在4-位置被取代的吗啉衍生物，通过取代的羰基或磺酰基团取代，并在3-位置通过一个可选择取代的吲哚-3-基甲基基团，作为选择性PI3激酶酶抑制剂，在医学上具有益处，例如在治疗炎症、自身免疫、心血管、神经退行性、代谢、肿瘤、疼痛或眼科疾病方面。
• Efficient synthesis of bromocyclopenta[<i>b</i>] indoles via a bromination - reduction sequence
  作者：Nicolas Lachance、Wing Yan Chan

  DOI：10.1002/jhet.5570400214

  日期：2003.3

  Substituted cyclopenta[b]indoles are selectively brominated in good yields with excess pyridine - Br2 charge-transfer complex (PyBr2) in a one-pot reaction to provide 5 and/or 7-bromoindoles. The mechanism involves the formation of an adduct (addition of bromine on the central double bond) which is subsequently reduced in situ with Zn and AcOH. A variety of functional groups in the cyclopentyl and

  在一锅反应中，用过量的吡啶-Br 2电荷转移络合物（PyBr 2）以高收率选择性地取代取代的环戊[ b ]吲哚，以提供5和/或7-溴吲哚。该机理涉及形成加合物（在中心双键上加成溴），其随后被Zn和AcOH原位还原。环戊基和苯环中的各种官能团是可容忍的。
• Cyclopentanoindoles, compositions containing such compounds and methods of treatment
  申请人：Merck Frosst Canada & Co.

  公开号：US06410583B1

  公开（公告）日：2002-06-25

  Substituted cyclopentanoindole derivatives are antagonists of prostaglandins, and as such are useful for the treatment of prostaglandin mediated diseases.

  替代环戊基吲哚衍生物是前列腺素拮抗剂，因此对于治疗前列腺素介导的疾病非常有用。

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