N1-(4-溴苯基)-3-溴丙酰胺 | 7661-10-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N1-(4-溴苯基)-3-溴丙酰胺
• 英文名称: 3-bromo-N-(4-bromophenyl)propanamide
• CAS: 7661-10-1
• 化学式: C₉H₉Br₂NO
• 分子量: 306.985
• InChiKey: ZFUGLAQIZREBFH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N1-(4-溴苯基)-3-溴丙酰胺 在 三氟甲磺酸 、 sodium t-butanolate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 13.0h， 生成 6-溴-2,3-二氢喹啉-4(1H)-酮
  参考文献：
  名称：

  [EN] NOVEL SUBSTITUTED TETRAHYDROQUINOLIN COMPOUNDS AS INDOLEAMINE 2,3-DIOXYGENASE (IDO) INHIBITORS
  [FR] NOUVEAUX COMPOSÉS DE TÉTRAHYDROQUINOLINE SUBSTITUÉS UTILISÉS EN TANT QU'INHIBITEURS DE L'INDOLÉAMINE 2,3-DIOXYGÉNASE (IDO)

  摘要：

  本文披露了式（I）的化合物，或其药学上可接受的盐（I）。本文还披露了所述化合物在潜在的治疗或预防IDO相关疾病或紊乱中的用途。本文还披露了包含所述化合物的组合物。本文进一步披露了所述组合物在潜在的治疗或预防IDO相关疾病或紊乱中的用途。

  公开号：

  WO2019089412A1
• 作为产物：
  描述：

  3-溴丙酰氯 、 4-溴苯胺 在 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 N1-(4-溴苯基)-3-溴丙酰胺
  参考文献：
  名称：

  [EN] NOVEL SUBSTITUTED TETRAHYDROQUINOLIN COMPOUNDS AS INDOLEAMINE 2,3-DIOXYGENASE (IDO) INHIBITORS
  [FR] NOUVEAUX COMPOSÉS DE TÉTRAHYDROQUINOLINE SUBSTITUÉS UTILISÉS EN TANT QU'INHIBITEURS DE L'INDOLÉAMINE 2,3-DIOXYGÉNASE (IDO)

  摘要：

  本文披露了式（I）的化合物，或其药学上可接受的盐（I）。本文还披露了所述化合物在潜在的治疗或预防IDO相关疾病或紊乱中的用途。本文还披露了包含所述化合物的组合物。本文进一步披露了所述组合物在潜在的治疗或预防IDO相关疾病或紊乱中的用途。

  公开号：

  WO2019089412A1

文献信息

• Solid Phase Synthesis of N-Alkyl Sulfonamides
  作者：Sharon Dankwardt、David Smith、John Porco Jr.、Cindy Nguyen

  DOI：10.1055/s-1997-5776

  日期：1997.7

  Polymer-supported sulfonamides were alkylated using alkyl halides in the presence of DBU or with alcohols via the Mitsunobu reaction.

  聚合物支撑的磺酰胺在 DBU 存在下使用烷基卤化物进行烷基化，或通过 Mitsunobu 反应与醇进行烷基化。
• Consequences of linker length alteration of the α7 nicotinic acetylcholine receptor (nAChR) agonist, SEN12333
  作者：Corinne Beinat、Samuel D. Banister、Saundra van Prehn、Munikumar Reddy Doddareddy、David Hibbs、Michael Sako、Mary Chebib、Thao Tran、Nour Al-Muhtasib、Yingxian Xiao、Michael Kassiou

  DOI：10.1016/j.bmcl.2012.02.052

  日期：2012.4

  A series of ligands based on SEN12333, containing either contracted or elongated alkyl chains, were synthesized and evaluated in molecular docking studies against a homology model of the alpha 7 nicotinic acetylcholine receptor (nAChR) subtype. The predicted binding of all ligands was highly similar, with the exception of the analog containing a 5 methylene unit spacer. However, in vitro competition binding assays revealed that the ligands possessed dissimilar binding affinities, with a K-i range of more than an order of magnitude (K-i = 0.50 to >10 mu M), and only SEN12333 itself exhibited functional activity at the alpha 7 nAChR. (C) 2012 Elsevier Ltd. All rights reserved.
• Harris, Stephen J.; Kinahan, Audrey M.; Meegan, Mary J., Journal of Chemical Research, Miniprint, 1994, # 9, p. 1832 - 1845
  作者：Harris, Stephen J.、Kinahan, Audrey M.、Meegan, Mary J.、Prendergast, Rhona C.

  DOI：——

  日期：——
• Further Optimization and Evaluation of Bioavailable, Mixed-Efficacy μ-Opioid Receptor (MOR) Agonists/δ-Opioid Receptor (DOR) Antagonists: Balancing MOR and DOR Affinities
  作者：Aubrie A. Harland、Larisa Yeomans、Nicholas W. Griggs、Jessica P. Anand、Irina D. Pogozheva、Emily M. Jutkiewicz、John R. Traynor、Henry I. Mosberg

  DOI：10.1021/acs.jmedchem.5b01270

  日期：2015.11.25

  In a previously described peptidomimetic series, we reported the development of bifunctional ?-opioid receptor (MOR) agonist and delta-opioid receptor (DOR) antagonist ligands with a lead compound that produced antinociception for 1 h after intraperitoneal administration in mice. In this paper, we expand on our original series by presenting two modifications, both of which were designed with the following objectives: (1) probing bioavailability and improving metabolic stability, (2) balancing affinities between MOR and DOR while reducing affinity and efficacy at the kappa-opioid receptor (KOR), and (3) improving in vivo efficacy. Here, we establish that, through N-acetylation of our original peptidomimetic series, we are able to improve DOR affinity and increase selectivity relative to KOR while maintaining the desired MOR agonist/DOR antagonist profile. From initial in vivo studies, one compound (14a) was found to produce dose-dependent antinociception after peripheral administration with an improved duration of action of longer than 3 h.
• NOVEL SUBSTITUTED TETRAHYDROQUINOLIN COMPOUNDS AS INDOLEAMINE 2,3-DIOXYGENASE (IDO) INHIBITORS
  申请人：Merck Sharp & Dohme Corp.

  公开号：EP3703692A1

  公开（公告）日：2020-09-09