ethyl (3-amino-5-nitrobenzothiophen)-2-carboxylate | 27697-60-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: ethyl (3-amino-5-nitrobenzothiophen)-2-carboxylate
• 英文别名: ethyl 3-amino-5-nitro[1]benzothiophene-2-carboxylate；ethyl 3-amino-5-nitrobenzo[b]thiophene-2-carboxylate；ethyl 3-amino-5-nitrobenzothiophene-2-carboxylate；ethyl 3-amino-5-nitro-1-benzothiophene-2-carboxylate
• CAS: 27697-60-5
• 化学式: C₁₁H₁₀N₂O₄S
• mdl: MFCD20922023
• 分子量: 266.277
• InChiKey: YQNPPODVURWWBM-UHFFFAOYSA-N

物化性质

• 沸点：
  455.9±40.0 °C(Predicted)
• 密度：
  1.466±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.181
• 拓扑面积：
  126
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl (3-amino-5-nitrobenzothiophen)-2-carboxylate 在 氯化亚砜 、 一水合肼 、 三乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 116.25h， 生成 N¹-[3-[2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl]-2,4-dioxo-1,2,3,4-tetrahydro[1]benzothieno[3,2-d]pyrimidin-8-yl]-N⁵-(phenylmethyl)pentanediamide
  参考文献：
  名称：

  High affinity ligands and potent antagonists for the α1D-adrenergic receptor. Novel 3,8-disubstituted [1]benzothieno[3,2-d]pyrimidine derivatives

  摘要：

  A new series of high affinity ligands and antagonists for the α1D-adrenergic receptor (AR) has been discovered. New molecules present a [1]benzothieno[3,2-d]pyrimidin-2,4(1H,3H)-dione or a [1]benzothieno[3,2-d]pyrimidin-4(3H)-one scaffold and bear a 2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl moiety in the 3-position and various amide substituents in the 8-position. In binding assays at the three human cloned α1A-, α1B-, and α1D-AR subtypes, they showed high affinity values, particularly for the α1D-AR subtype. Compound 22 (RX18), N(1)-methyl-N(5)-[3-[2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl]-2,4-dioxo-1,2,3,4-tetrahydro[1]benzothieno[3,2-d]pyrimidin-8-yl]-N(1)-(phenylmethyl)pentanediamide, was the most interesting in the series displaying very high affinity (pKi = 10.25) and potent antagonism (pKb = 9.15) when tested in a functional assay at the α1D-AR.

  DOI：

  10.1016/j.ejmech.2014.06.057
• 作为产物：
  描述：

  2-氟苯腈 在 硫酸 、 硝酸 、 sodium hydride 作用下， 以 二甲基亚砜 、 mineral oil 为溶剂， 反应 5.33h， 生成 ethyl (3-amino-5-nitrobenzothiophen)-2-carboxylate
  参考文献：
  名称：

  Synthesis, antiproliferative activity, and in silico insights of new 3-benzoylamino-benzo[b]thiophene derivatives

  摘要：

  A new series of 3-benzoylamino-5-imidazol-5-yl-benzo[b]thiophenes and the parent amino derivatives were synthesized and screened as antitumor agents. All tested compounds showed concentration-dependent antiproliferative activity profile against HeLa cell line, exhibiting GI50 values in the low micromolar range. The most active compounds were tested in cell cycle perturbation experiments. A rapid accumulation of cells in the G2/M phase, with a concomitant reduction of cells in both the S and G0/G1 phases, was observed, suggesting that cell exposure to selected derivatives produces mitotic failure. To rationalize the biological results, the 3-benzoylamino-benzo[b]thiophenes were analyzed through the in silk VLAK protocol. Compounds presenting the 3,4,5-trimethoxy-benzoyl moiety were in silica classified as potential antimitotic agents or topoisomerase II inhibitors, in good agreement with the biological studies. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.12.002

文献信息

• Synthesis and Structure-Activity Relationship Studies of 2-(1,3,4-Oxadiazole-2(3<i>H</i>)-thione)-3-amino-5-arylthieno[2,3-<i>b</i>]pyridines as Inhibitors of DRAK2
  作者：Piotr Leonczak、Ling-Jie Gao、Anna Teresa Ramadori、Eveline Lescrinier、Jef Rozenski、Steven De Jonghe、Piet Herdewijn

  DOI：10.1002/cmdc.201402234

  日期：2014.11

  recent years, DAPK‐related apoptosis‐inducing protein kinase 2 (DRAK2) has emerged as a promising target for the treatment of a variety of autoimmune diseases and for the prevention of graft rejection after organ transplantation. However, medicinal chemistry optimization campaigns for the discovery of novel small‐molecule inhibitors of DRAK2 have not yet been published. Screening of a proprietary compound

  近年来，DAPK相关的凋亡诱导蛋白激酶2（DRAK2）已成为治疗各种自身免疫性疾病和预防器官移植后移植排斥的有希望的靶标。但是，尚未发现用于发现DRAK2新型小分子抑制剂的药物化学优化方案。导致了苯并噻吩类似物的发现专有化合物文库的筛选，其中显示的亲和常数（ķ d 0.25μ）值中号。芯支架的变化时，可以得到一系列5- arylthieno [2,3-的取代模式的b ]与强的结合亲和力的吡啶（ķ d = 0.008μ中号代表最有力的代表）。这些化合物还显示出在功能生化DRAK2酶测定有前途的活性，与IC 50值的0.029μ中号为最有效的同类。最有效的化合物的选择性分析表明，它们在DAPK激酶家族中缺乏选择性。但是，效力较低的类似物之一是DRAK2的选择性配体，可以用作合成选择性有效的DRAK2抑制剂的起点。
• Tricyclic compounds capable of inhibiting tyrosine kinases of the
  申请人：Warner-Lambert Company

  公开号：US05679683A1

  公开（公告）日：1997-10-21

  Novel 4-substituted amino benzothieno\x9b3,2-d!pyrimidine and 4-substituted amino\x9b2,3-d!pyrimidine inhibitors of epidermal growth factor receptor family of tyrosine kinases are described, as well as pharmaceutical compositions of the same, which are useful in treating proliferative diseases such as cancer, synovial pannus invasion in arthritis, psoriasis, vascular restenosis and angiogenesis and additionally useful in the treatment of pancreatitis and kidney disease as well as a contraceptive agent.

  描述了一种新型的4-取代氨基苯并噻吩\9b3,2-d!嘧啶和4-取代氨基\9b2,3-d!嘧啶表皮生长因子受体家族的酪氨酸激酶抑制剂，以及相应的药物组合物，用于治疗增殖性疾病，如癌症、关节炎中的滑膜潘纳斯侵袭、牛皮癣、血管再狭窄和血管生成，此外还可用于胰腺炎和肾病的治疗，以及避孕剂。
• Structure of ethyl(3-amino-5-nitrobenzo[b]thiophen)-2-carboxylate
  作者：Giancarlo Pelizzi、Paola Vicini

  DOI：10.1007/bf01161074

  日期：1991.10

  The title compound was obtained as main product by the reaction of 3-chloro-5-nitro-1,2-benzisothiazole with diethyl malonate in sodium ethoxide. It crystallizes in the monoclinic space group P2(1)/n with a = 12.143(5), b = 11.172(4), c = 8.567(3) angstrom, beta = 95.51(2)-degrees, Z = 4. The structure was solved by direct methods and refined by full-matrix least-squares to a final R value of 0.035 for 1217 reflections. The entire molecule is substantially planar except for the terminal methyl group. The amino group is involved in intra- and intermolecular hydrogen bonding.
• TRICYCLIC COMPOUNDS CAPABLE OF INHIBITING TYROSINE KINASES OF THE EPIDERMAL GROWTH FACTOR RECEPTOR FAMILY
  申请人：WARNER-LAMBERT COMPANY

  公开号：EP0741711A1

  公开（公告）日：1996-11-13
• US5679683A
  申请人：——

  公开号：US5679683A

  公开（公告）日：1997-10-21