4-((2-methylpiperidin-1-yl)sulfonyl)aniline | 109099-69-6

• 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-((2-methylpiperidin-1-yl)sulfonyl)aniline
• 英文别名: 4-[(2-Methylpiperidin-1-yl)sulfonyl]aniline；4-(2-methylpiperidin-1-yl)sulfonylaniline
• CAS: 109099-69-6
• 化学式: C₁₂H₁₈N₂O₂S
• mdl: MFCD01055485
• 分子量: 254.353
• InChiKey: YCXPHUHJDQRZRT-UHFFFAOYSA-N

物化性质

• 熔点：
  109-117 °C
• 沸点：
  420.7±47.0 °C(Predicted)
• 密度：
  1.228±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  71.8
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2935009090

反应信息

• 作为反应物：
  描述：

  苯酐 、 4-((2-methylpiperidin-1-yl)sulfonyl)aniline 以 二甲基亚砜 为溶剂， 以77%的产率得到2-(4-((2-methylpiperidin-1-yl)sulfonyl)phenyl)isoindoline-1,3-dione
  参考文献：
  名称：

  Synthesis and structure–activity relationships for 1-(4-(piperidin-1-ylsulfonyl)phenyl)pyrrolidin-2-ones as novel non-carboxylate inhibitors of the aldo-keto reductase enzyme AKR1C3

  摘要：

  High expression of the aldo-keto reductase enzyme AKR1C3 in the human prostate and breast has implicated it in the development and progression of leukemias and of prostate and breast cancers. Inhibitors are thus of interest as potential drugs. Most inhibitors of AKR1C3 are carboxylic acids, whose transport into cells is likely dominated by carrier-mediated processes. We describe here a series of (piperidinosulfonamidophenyl)pyrrolidin-2-ones as potent (<100 nM) and isoform-selective non-carboxylate inhibitors of AKR1C3. Structure-activity relationships identified the sulfonamide was critical, and a crystal structure showed the 2-pyrrolidinone does not interact directly with residues in the oxyanion hole. Variations in the position, co-planarity or electronic nature of the pyrrolidinone ring severely diminished activity, as did altering the size or polarity of the piperidino ring. There was a broad correlation between the enzyme potencies of the compounds and their effectiveness at inhibiting AKR1C3 activity in cells. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.01.047
• 作为产物：
  描述：

  2-甲基哌啶 在 palladium 10% on activated carbon 、 氢气 、 三乙胺 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 20.0 ℃ 、506.66 kPa 条件下， 反应 8.0h， 生成 4-((2-methylpiperidin-1-yl)sulfonyl)aniline
  参考文献：
  名称：

  Synthesis and structure–activity relationships for 1-(4-(piperidin-1-ylsulfonyl)phenyl)pyrrolidin-2-ones as novel non-carboxylate inhibitors of the aldo-keto reductase enzyme AKR1C3

  摘要：

  High expression of the aldo-keto reductase enzyme AKR1C3 in the human prostate and breast has implicated it in the development and progression of leukemias and of prostate and breast cancers. Inhibitors are thus of interest as potential drugs. Most inhibitors of AKR1C3 are carboxylic acids, whose transport into cells is likely dominated by carrier-mediated processes. We describe here a series of (piperidinosulfonamidophenyl)pyrrolidin-2-ones as potent (<100 nM) and isoform-selective non-carboxylate inhibitors of AKR1C3. Structure-activity relationships identified the sulfonamide was critical, and a crystal structure showed the 2-pyrrolidinone does not interact directly with residues in the oxyanion hole. Variations in the position, co-planarity or electronic nature of the pyrrolidinone ring severely diminished activity, as did altering the size or polarity of the piperidino ring. There was a broad correlation between the enzyme potencies of the compounds and their effectiveness at inhibiting AKR1C3 activity in cells. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.01.047

文献信息

• [EN] REMODILINS FOR AIRWAY REMODELING AND ORGAN FIBROSIS<br/>[FR] REMODILINES POUR LE REMODELAGE DES VOIES RESPIRATOIRES ET FIBROSE D'ORGANE
  申请人：UNIV CHICAGO

  公开号：WO2020206109A1

  公开（公告）日：2020-10-08

  Disclosed herein is a class of molecules termed remodilins that are effective in treating asthma, pulmonary fibrosis, and associated disorders. The molecules ameliorate asthma and pulmonary fibrosis symptoms by various mechanisms, including inhibiting airway smooth muscle contractile protein accumulation, reducing airway constrictor hyperresponsiveness, inhibiting bronchial fibroblast transformation into myofibroblasts, and/or treating or preventing airway or pulmonary fibrosis.

  本文披露了一类分子，称为remodilins，它们在治疗哮喘、肺纤维化及相关疾病方面具有有效性。这些分子通过各种机制改善哮喘和肺纤维化症状，包括抑制气道平滑肌收缩蛋白的积累，减少气道收缩过度反应，抑制支气管成纤维细胞向肌成纤维细胞的转化，和/或治疗或预防气道或肺纤维化。
• [EN] REMODILINS TO PREVENT OR TREAT CANCER METASTASIS, GLAUCOMA, AND HYPOXIA<br/>[FR] REMODILINES POUR PRÉVENIR OU TRAITER DES MÉTASTASES CANCÉREUSES, LE GLAUCOME ET L'HYPOXIE
  申请人：UNIV CHICAGO

  公开号：WO2020206118A1

  公开（公告）日：2020-10-08

  Disclosed herein is a class of molecules termed remodilins that inhibit serum response factor (SRF). By inhibiting SRF, a number of downstream pathways can be targeted. The remodilins can be used to treat glaucoma, inhibit tumor cell growth, inhibit tumor metastasis, inhibit hypoxia-induced response, and/or reduce cellular metabolism.

  本文披露了一类分子，被称为抑制血清反应因子（SRF）的remodilins。通过抑制SRF，可以针对许多下游途径。Remodilins可用于治疗青光眼，抑制肿瘤细胞生长，抑制肿瘤转移，抑制缺氧诱导反应，和/或减少细胞代谢。
• Potent Non-Nucleoside Inhibitors of the Measles Virus RNA-Dependent RNA Polymerase Complex
  作者：Aiming Sun、Jeong-Joong Yoon、Yan Yin、Andrew Prussia、Yutao Yang、Jaeki Min、Richard K. Plemper、James P. Snyder

  DOI：10.1021/jm701239a

  日期：2008.7

  Measles virus (MV) is one of the most infectious pathogens known. In spite of the existence of a vaccine, approximately 350000 deaths/year result from MV or associated complications. Antimeasles compounds Could conceivably diminish these statistics and provide a therapy that complements vaccine treatment. We recently described a high-throughput screening hit compound 1 (16677) against MV-infected cells with the capacity to eliminate viral reproduction at 250 nM by inhibiting the action of the virus's RNA-dependent RNA polymerase complex (RdRp). The compound, 1-methyl-3-(trifluoroi-nethyl)-N-[4-sulfonylphenyl]-1H-pyrazole-5-carboxamide, 1 carries a critical CF3 moiety on the 1,2-pyrazole ring. Elaborating on the preliminary structure-activity (SAR) study, the present work presents the synthesis and SAR of a much broader range of low nanomolar nonpeptidic MV inhibitors and speculates on the role of the CF3 functionality.
• PLANT PRIMING COMPOSITIONS AND METHODS OF USE THEREOF
  申请人：Zero Gravity Solutions, Inc.

  公开号：EP4021184A1

  公开（公告）日：2022-07-06
• [EN] PLANT PRIMING COMPOSITIONS AND METHODS OF USE THEREOF<br/>[FR] COMPOSITIONS D'AMORÇAGE DE PLANTE ET LEURS PROCÉDÉS D'UTILISATION
  申请人：ZERO GRAVITY SOLUTIONS INC

  公开号：WO2021041969A1

  公开（公告）日：2021-03-04

  Provided herein are compositions and methods to improve plant resistance to abiotic and biotic stress, thereby improving crop yield. Provided herein are compositions including zinc, copper, and an acid, where the acid is selected from citric acid, sulfuric acid, oxalic acid, humic acid, fulvic acid, boric acid, acetic acid, and a combination thereof. Certain embodiments optionally include ammonium sulfate. Compositions described herein have plant priming activity where the plant's defenses against abiotic and biotic stress are boosted.