chloro-acetic acid-(1,2,3,4-tetrahydro-[1]naphthylamide) | 127761-16-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: chloro-acetic acid-(1,2,3,4-tetrahydro-[1]naphthylamide)
• 英文别名: Chlor-essigsaeure-(1,2,3,4-tetrahydro-[1]naphthylamid)；2-chloroacetamido-tetralin；2-chloro-N-(1,2,3,4-tetrahydronaphthalen-1-yl)acetamide
• CAS: 127761-16-4
• 化学式: C₁₂H₁₄ClNO
• mdl: MFCD03150772
• 分子量: 223.702
• InChiKey: SLQUITRGZWAZBX-UHFFFAOYSA-N

物化性质

• 沸点：
  418.9±34.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.416
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 危险等级：
  IRRITANT

反应信息

• 作为反应物：
  描述：

  5-硝基-2-糠酸 、 chloro-acetic acid-(1,2,3,4-tetrahydro-[1]naphthylamide) 在 4-二甲氨基吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以45%的产率得到[2-Oxo-2-(1,2,3,4-tetrahydronaphthalen-1-ylamino)ethyl] 5-nitrofuran-2-carboxylate
  参考文献：
  名称：

  Structural and biochemical study on the inhibitory activity of derivatives of 5-nitro-furan-2-carboxylic acid for RNase H function of HIV-1 reverse transcriptase

  摘要：

  Rapid emergence of drug-resistant variants is one of the most serious problems in chemotherapy for HIV-1 infectious diseases. Inhibitors acting on a target not addressed by approved drugs are of great importance to suppress drug-resistant viruses. HIV-1 reverse transcriptase has two enzymatic functions, DNA polymerase and RNase H activities. The RNase H activity is an attractive target for a new class of antiviral drugs. On the basis of the hit chemicals found in our previous screening with 20,000 small molecular-weight compounds, we synthesized derivatives of 5-nitro-furan-2-carboxylic acid. Inhibition of RNase H enzymatic activity was measured in a biochemical assay with real-time monitoring of florescence emission from the digested RNA substrate. Several derivatives showed higher inhibitory activities that those of the hit chemicals. Modulation of the 5-nitro-furan-2-carboxylic moiety resulted in a drastic decrease in inhibitory potency. In contrast, many derivatives with modulation of other parts retained inhibitory activities to varying degrees. These findings suggest the binding mode of active derivatives, in which three oxygen atoms aligned in a straight form at the nitro-furan moiety are coordinated to two divalent metal ions located at RNase H reaction site. Hence, the nitro-furan-carboxylic moiety is one of the critical scaffolds for RNase H inhibition. Of note, the RNase H inhibitory potency of a derivative was improved by 18-fold compared with that of the original hit compound, and no significant cytotoxicity was observed for most of the derivatives showing inhibitory activity. Since there is still much room for modification of the compounds at the part opposite the nitro-furan moiety, further chemical conversion will lead to improvement of compound potency and specificity. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.12.011
• 作为产物：
  描述：

  1,2,3,4-四氢-1-萘胺 、 氯乙酰氯 在 sodium hydroxide 作用下， 生成 chloro-acetic acid-(1,2,3,4-tetrahydro-[1]naphthylamide)
  参考文献：
  名称：

  Adank et al., Rendiconti - Istituto superiore di sanita, 1953, vol. 16, p. 133,136

  摘要：

  DOI：

文献信息

• Substituted 2-amidotetralins as melatonin agonists and antagonists
  申请人：NORTHWESTERN UNIVERSITY

  公开号：EP0420064A2

  公开（公告）日：1991-04-03

  The present invention relates generally to compounds having melatonin receptor activities and in particular to substituted 2-amidotetralin derivatives; to pharmaceutical preparations comprising such compounds; and to methods for using these compounds as therapeutic and diagnostic reagents.

  本发明一般涉及具有褪黑激素受体活性的化合物，特别是取代的 2-脒基四氢萘衍生物；涉及包含这些化合物的药物制剂；以及涉及将这些化合物用作治疗和诊断试剂的方法。
• ARMSTRONG, DANIEL W.;LI, WEIYONG;STALCUP, APRYLL M.;SECOR, HENRY V.;IZAC,+, ANAL. CHIM. ACTA , 234,(1990) N, C. 365-380
  作者：ARMSTRONG, DANIEL W.、LI, WEIYONG、STALCUP, APRYLL M.、SECOR, HENRY V.、IZAC,+

  DOI：——

  日期：——
• METHODS OF CORRECTING IMBALANCE BETWEEN BONE RESORPTION AND BONE FORMATION AND KITS AND COMPOSITIONS THEREFOR
  申请人：Chu Sainte-justine

  公开号：EP2120912A1

  公开（公告）日：2009-11-25
• METHOD OF CORRECTING IMBALANCE BETWEEN BONE RESORPTION AND BONE FORMATION AND KITS AND COMPOSITIONS THEREFOR
  申请人：Moreau Alain

  公开号：US20100029567A1

  公开（公告）日：2010-02-04

  Compounds, methods, uses, compositions, kits and packages for the treatment of imbalance between bone resorption and bone formation, based on uses of 4-phenyl-2 propionamidotetralin (4-P-PDOT) and analogs, derivatives, prodrugs, precursors thereof, and salts thereof, are described.
• US5071875A
  申请人：——

  公开号：US5071875A

  公开（公告）日：1991-12-10