5-nitro-4-dimethylamino-2-thiophenecarboxaldehyde | 276888-76-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: 5-nitro-4-dimethylamino-2-thiophenecarboxaldehyde
• 英文别名: 4-(Dimethylamino)-5-nitrothiophene-2-carbaldehyde
• CAS: 276888-76-7
• 化学式: C₇H₈N₂O₃S
• 分子量: 200.218
• InChiKey: ILNGPVDKBRMULQ-UHFFFAOYSA-N

物化性质

• 熔点：
  150-153 °C
• 沸点：
  353.2±42.0 °C(Predicted)
• 密度：
  1.425±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  94.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-nitro-4-dimethylamino-2-thiophenecarboxaldehyde 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.83h， 以82%的产率得到5-nitro-4-dimethylamino-2-hydroxymethylthiophene
  参考文献：
  名称：

  Synthesis and Evaluation of Nitroheterocyclic Phosphoramidates as Hypoxia-Selective Alkylating Agents

  摘要：

  A series of novel nitroheterocyclic phosphoramidates has been prepared, and the cytotoxicity of these compounds has been evaluated in clonogenic assays against B16, wild-type and cyclophosphamide-resistant MCF-7, and HT-29 cells under aerobic conditions and HT-29 cells under hypoxic conditions. All compounds were comparable in toxicity to wild-type and resistant MCF-7 cells and were also selectively toxic to HT-29 cells under hypoxic conditions (selectivity ratios 1.7 to >20). Analogues lacking the nitro group were not cytotoxic. Electron-withdrawing substituents increased cytotoxicity under aerobic conditions and thereby decreased hypoxic selectivity. In contrast, an electron-donating substituent markedly decreased both aerobic and hypoxic cytotoxicity but enhanced hypoxic selectivity. Chemical reduction of the nitro group resulted in rapid expulsion of the cytotoxic phosphoramide mustard. The most potent of these compounds show significant cytotoxicity under both aerobic and hypoxic conditions.

  DOI：

  10.1021/jm0001020
• 作为产物：
  描述：

  4-bromo-2-thiophenecarboxaldehyde diacetate 在 硝酸 、 乙酸酐 、 三乙胺 作用下， 以 氯仿 、 溶剂黄146 为溶剂， 反应 4.5h， 生成 5-nitro-4-dimethylamino-2-thiophenecarboxaldehyde
  参考文献：
  名称：

  Synthesis and Evaluation of Nitroheterocyclic Phosphoramidates as Hypoxia-Selective Alkylating Agents

  摘要：

  A series of novel nitroheterocyclic phosphoramidates has been prepared, and the cytotoxicity of these compounds has been evaluated in clonogenic assays against B16, wild-type and cyclophosphamide-resistant MCF-7, and HT-29 cells under aerobic conditions and HT-29 cells under hypoxic conditions. All compounds were comparable in toxicity to wild-type and resistant MCF-7 cells and were also selectively toxic to HT-29 cells under hypoxic conditions (selectivity ratios 1.7 to >20). Analogues lacking the nitro group were not cytotoxic. Electron-withdrawing substituents increased cytotoxicity under aerobic conditions and thereby decreased hypoxic selectivity. In contrast, an electron-donating substituent markedly decreased both aerobic and hypoxic cytotoxicity but enhanced hypoxic selectivity. Chemical reduction of the nitro group resulted in rapid expulsion of the cytotoxic phosphoramide mustard. The most potent of these compounds show significant cytotoxicity under both aerobic and hypoxic conditions.

  DOI：

  10.1021/jm0001020

文献信息

• [EN] OXAZOLIDINONE DERIVATIVES AS ANTIMICROBIALS<br/>[FR] DERIVES D'OXAZOLIDINONES EN TANT QU'AGENTS ANITMICROBIENS
  申请人：RANBAXY LAB LTD

  公开号：WO2004069816A1

  公开（公告）日：2004-08-19

  The present invention relates to certain substituted phenyl oxazolidinones of the formula h wherein T is a ring and to the processes for the synthesis of the same. The compounds are useful antimicrobial agents, effective against a number of human and veterinary pathogens, including gram-positive aerobic bacteria such as multiply-resistant staphylococci, streptococci and enterococci as well as anaerobic organisms such as Bactericides spp. and Clostridia spp. species, and acid fast organisms such as Mycobacterium tuberculosis, Mycobacterium avium and Mycobacterium tuberculosis, Mycobacterium avium and Mycobacterium spp.

  本发明涉及某些带有取代基的苯基噁唑烷酮，其化学式为h，其中T是一个环，并涉及其合成过程。这些化合物是有用的抗微生物剂，对许多人类和兽医病原体有效，包括革兰氏阳性厌氧细菌，如多重耐药葡萄球菌、链球菌和肠球菌，以及厌氧生物，如杆菌属和梭菌属物种，以及耐酸生物，如结核分枝杆菌、分枝杆菌和结核分枝杆菌、分枝杆菌和分枝杆菌属。
• OXAZOLIDINONE DERIVATIVES AS POTENTIAL ANTIMICROBIALS
  申请人：RANBAXY LABORATORIES, LTD.

  公开号：EP1409464A1

  公开（公告）日：2004-04-21
• OXAZOLIDINONE DERIVATIVES AS ANTIMICROBIALS
  申请人：RANBAXY LABORATORIES, LTD.

  公开号：EP1594852A1

  公开（公告）日：2005-11-16
• [EN] OXAZOLIDINONE DERIVATIVES AS POTENTIAL ANTIMICROBIALS<br/>[FR] DERIVES D'OXAZOLIDINONE UTILISES COMME ANTIMICROBIENS POTENTIELS
  申请人：RANBAXY LAB LTD

  公开号：WO2003008389A1

  公开（公告）日：2003-01-30

  The present invention relates to certain substituted phenyl oxazolidinones and to processes for the synthesis of the same. This invention also relates to pharmaceutical compositions containing the compounds of the present invention as antimicrobials. The compounds are useful antimicrobial agents, effective against a number of human and veterinary pathogens, including gram-positive aerobic bacteria such as multiply-resistant staphylococci, streptococci and enterococci as well as anaerobic organisms such as Bacteroides spp. and Clostridium spp. species, and acid fast organisms such as Mycobacterium tuberculosis, Mycobacterium avium and Mycobacterium spp.
• Synthesis and Evaluation of Nitroheterocyclic Phosphoramidates as Hypoxia-Selective Alkylating Agents
  作者：Richard F. Borch、Jiwen Liu、James P. Schmidt、Joseph T. Marakovits、Carolyn Joswig、Jerry J. Gipp、R. Timothy Mulcahy

  DOI：10.1021/jm0001020

  日期：2000.6.1

  A series of novel nitroheterocyclic phosphoramidates has been prepared, and the cytotoxicity of these compounds has been evaluated in clonogenic assays against B16, wild-type and cyclophosphamide-resistant MCF-7, and HT-29 cells under aerobic conditions and HT-29 cells under hypoxic conditions. All compounds were comparable in toxicity to wild-type and resistant MCF-7 cells and were also selectively toxic to HT-29 cells under hypoxic conditions (selectivity ratios 1.7 to >20). Analogues lacking the nitro group were not cytotoxic. Electron-withdrawing substituents increased cytotoxicity under aerobic conditions and thereby decreased hypoxic selectivity. In contrast, an electron-donating substituent markedly decreased both aerobic and hypoxic cytotoxicity but enhanced hypoxic selectivity. Chemical reduction of the nitro group resulted in rapid expulsion of the cytotoxic phosphoramide mustard. The most potent of these compounds show significant cytotoxicity under both aerobic and hypoxic conditions.