6-carbamoylnaphthalene-2-carboxylic acid | 149505-84-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 6-carbamoylnaphthalene-2-carboxylic acid
• 英文别名: 6-carbamoyl-2-naphthoic acid；naphthalene-2,6-dicarboxylic acid monoamide
• CAS: 149505-84-0
• 化学式: C₁₂H₉NO₃
• 分子量: 215.208
• InChiKey: YUEBLCOCHGDFRH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  80.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-carbamoylnaphthalene-2-carboxylic acid 、 4-(3-甲氧基苯基)苯胺 在 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 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 48.25h， 以10%的产率得到N(2)-(3'-methoxybiphenyl-4-yl)naphthalene-2,6-dicarboxamide
  参考文献：
  名称：

  Synthesis and evaluation of non-basic inhibitors of urokinase-type plasminogen activator (uPA)

  摘要：

  Recent drug discovery programs targeting urokinase plasminogen activator (uPA) have resulted in non-peptidic inhibitors consisting of amidine or guanidine functional groups attached to aromatic or heteroaromatic scaffolds. There is a general problem of poor oral bioavailability of these charged inhibitors. In this paper, we report the synthesis and evaluation of a series of naphthamide and naphthalene sulfonamides as uPA inhibitors containing non-basic groups as substitute for amidine or guanidine groups. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.12.040
• 作为产物：
  描述：

  2,6-萘二羧酸二甲酯 在 氯化亚砜 、 lithium hydroxide monohydrate 、 氨 、 potassium hydroxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 水 、 甲苯 为溶剂， 生成 6-carbamoylnaphthalene-2-carboxylic acid
  参考文献：
  名称：

  Synthesis and evaluation of non-basic inhibitors of urokinase-type plasminogen activator (uPA)

  摘要：

  Recent drug discovery programs targeting urokinase plasminogen activator (uPA) have resulted in non-peptidic inhibitors consisting of amidine or guanidine functional groups attached to aromatic or heteroaromatic scaffolds. There is a general problem of poor oral bioavailability of these charged inhibitors. In this paper, we report the synthesis and evaluation of a series of naphthamide and naphthalene sulfonamides as uPA inhibitors containing non-basic groups as substitute for amidine or guanidine groups. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.12.040

文献信息

• Cyclic imino derivatives and pharmaceutical compositions containing them
  申请人：Karl Thomae GmbH

  公开号：US05541343A1

  公开（公告）日：1996-07-30

  The invention relates to cyclic imino compounds which have, inter alia, valuable pharmacological properties, especially inhibitory effects on cell aggregation, pharmaceutical compositions which contain these compounds and processes for preparing them.

  这项发明涉及具有有价值的药理特性，特别是对细胞聚集具有抑制作用的环亚胺化合物，包含这些化合物的药物组合物以及制备它们的方法。
• Urokinase inhibitors
  申请人：——

  公开号：US20010049374A1

  公开（公告）日：2001-12-06

  Compounds having the formula 1 are inhibitors of urokinase and are useful in the treatment of diseases in which urokinase plays a role. Also disclosed are urokinase-inhibiting compositions and a method of inhibiting urokinase in a mammal.

  化合物的化学式为1，它们是尿激酶抑制剂，在尿激酶发挥作用的疾病治疗中有用。还披露了抑制尿激酶的组合物和一种在哺乳动物中抑制尿激酶的方法。
• 2-ACYLAMINOTHIAZOLE DERIVATIVE OR SALT THEREOF
  申请人：SUGASAWA Keizo

  公开号：US20100222361A1

  公开（公告）日：2010-09-02

  A 2-acylaminothiazole derivative or a pharmaceutically acceptable salt thereof having an excellent effect of proliferating human c-mpl-Ba/F3 cells and an activity of increasing platelets based on the effect of promoting the formation of megakaryocytic colonies. A compound or a pharmaceutically acceptable salt thereof useful in treating thrombocytopenia.

  一种2-酰氨基噻唑衍生物或其药学上可接受的盐，具有促进人类c-mpl-Ba/F3细胞增殖的卓越效果，并且基于促进巨核细胞集落形成的作用，具有增加血小板的活性。一种化合物或其药学上可接受的盐，可用于治疗血小板减少症。
• METHODS FOR THE IDENTIFICATION AND CHARACTERIZATION OF HDAC INTERACTING COMPOUNDS
  申请人：Drewes Gerard

  公开号：US20130071854A1

  公开（公告）日：2013-03-21

  The present invention relates to methods for the identification and characterization (e.g. selectivity profiling) of HDAC interacting compounds using protein preparations derived from cells endogenously expressing HDACs or cell preparations containing said HDACs.

  本发明涉及使用从内源表达HDAC的细胞中得到的蛋白质制备或含有该HDAC的细胞制备，对HDAC相互作用化合物进行鉴定和表征（例如选择性分析）的方法。
• Hypoxia-Activated Prodrugs: Substituent Effects on the Properties of Nitro <i>seco</i>-1,2,9,9a-Tetrahydrocyclopropa[<i>c</i>]benz[<i>e</i>]indol-4-one (nitroCBI) Prodrugs of DNA Minor Groove Alkylating Agents
  作者：Moana Tercel、Graham J. Atwell、Shangjin Yang、Ralph J. Stevenson、K. Jane Botting、Maruta Boyd、Eileen Smith、Robert F. Anderson、William A. Denny、William R. Wilson、Frederik B. Pruijn

  DOI：10.1021/jm901202b

  日期：2009.11.26

  Nitrochloromethylbenzindolines (nitroCBIs) are a new class of hypoxia-activated prodrugs for antitumor therapy. The recently reported prototypes undergo hypoxia-selective metabolism to form potent DNA minor groove alkylating agents and are selectively toxic to some but not all hypoxic tumor cell lines. Here we report a series of 31 analogues that bear an extra electron-withdrawing substituent that serves to raise the one-electron reduction potential of the nitroCBI. We identify a subset of compounds, those with a basic side chain and sulfonamide or carboxamide substituent, that have consistently high hypoxic selectivity. The best of these, with a 7-sulfonamide substituent, displays hypoxic cytotoxicity ratios of 275 and 330 in Skov3 and HT29 human tumor cell lines, respectively. This compound (28) is efficiently and selectively metabolized to the corresponding aminoCBI, is selectively cytotoxic tinder hypoxia in all 11 cell lines examined, and demonstrates activity against hypoxic tumor cells in a human tumor xenograft in vivo.