2-氨基-4,5,6,7-四氢-1-苯并噻吩-3-羧酸丙酯 | 302561-09-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 中文名称: 2-氨基-4,5,6,7-四氢-1-苯并噻吩-3-羧酸丙酯
• 中文别名: 2-氨基-4,5,6,7-四氢苯并噻吩-3-羧酸丙酯；2-氨基-4,5,6,7-四氢苯并噻吩-3-甲酸丙酯；2-氨基-4,5,6,7-四氢-1-苯并噻吩-3-甲酸丙酯
• 英文名称: propyl 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate
• 英文别名: 2-amino-4,5,6,7-tetrahydro-benzo[b]thiophene-3-carboxylic acid propyl ester；Propyl 2-amino-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxylate
• CAS: 302561-09-7
• 化学式: C₁₂H₁₇NO₂S
• mdl: MFCD00449584
• 分子量: 239.338
• InChiKey: PADGJVHWIWPICX-UHFFFAOYSA-N

物化性质

• 沸点：
  417.0±45.0 °C(Predicted)
• 密度：
  1.203±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.583
• 拓扑面积：
  80.6
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  2-氨基-4,5,6,7-四氢-1-苯并噻吩-3-羧酸丙酯 在 吡啶 、 三乙胺 作用下， 以 乙醚 为溶剂， 反应 6.0h， 生成 isopropyl 2-[(piperidin-1-ylacetyl)amino]-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxylate
  参考文献：
  名称：

  [EN] ANTHELMINTIC AND INSECTICIDAL THIOPHENE DERIVATIVES
  [FR] VERMIFUGES ET INSECTICIDES A BASE DE DERIVES THIOPHENIQUES

  摘要：

  新的含有噻吩衍生物作为活性成分的驱虫剂组合物被揭示。

  公开号：

  WO2003101979A1
• 作为产物：
  描述：

  氰乙酸正丙酯 、 环己酮 在 1,2,3,4,5,6,7,8-八硫杂环辛烷 、 二乙胺 作用下， 以 甲醇 、 乙醇 为溶剂， 以91%的产率得到2-氨基-4,5,6,7-四氢-1-苯并噻吩-3-羧酸丙酯
  参考文献：
  名称：

  N - Aryl- N '-(thiophen-2-yl) thiourea衍生物作为潜在癌症免疫治疗的新型特异性人 TLR1/2 激动剂的设计、合成和结构-活性关系

  摘要：

  之前对 1000 万种化合物的虚拟筛选产生了两种新的非脂肽样化学型作为 TLR2 激动剂。在此，我们介绍了我们最初命中的 1-苯基-3-(噻吩-2-基) 脲的化学优化，这导致将 SMU-C80 (EC 50 = 31.02 ± 1.01 nM)鉴定为 TLR2 特异性生物活性提高 370 倍的激动剂。机理研究表明，SMU-C80 通过 TLR1/2 募集接头蛋白 MyD88 并触发 NF-κB 通路以从人类而非鼠类细胞中释放细胞因子，例如 TNF-α 和 IL-1β。据我们所知，它是迄今为止报道的第一个物种特异性 TLR1/2 激动剂。此外，SMU-C80 增加了离体T、B 和 NK 细胞的百分比并激活免疫细胞，从而抑制体外癌细胞的生长。总之，我们获得了一种高效且特异的人 TLR1/2 激动剂，它通过 MyD88 和 NF-κB 途径起作用，促进细胞因子的释放和免疫细胞的同时激活，进而影响癌细胞的凋亡。

  DOI：

  10.1021/acs.jmedchem.0c02266

文献信息

• Synthesis of urea analogues bearing N-alkyl-N'-(thiophen-2-yl) scaffold and evaluation of their innate immune response to toll-like receptors
  作者：Zhipeng Chen、Xiaohong Cen、Junjie Yang、Zhiman Lin、Meihuan Liu、Kui Cheng

  DOI：10.1016/j.ejmech.2019.02.067

  日期：2019.5

  Previous high throughput virtual screening of 10 million-compound and following cell based validation led to the discovery of a novel, nonlipopeptide-like chemotype ZINC 6662436, as toll-like receptor 2 (TLR2) agonists. In this report, compounds belonging to four areas of structural modification of ZINC6662436 were evaluated for biological activity using human HEK-Blue TLR2 reporter cells, and human THP-1 monocytic cells, yield SMU-C13 as an optimized, direct and high potent (EC50 = 160 nM) agonist of human TLR2. Moreover, preliminary mechanism studies indicated that SMU-C13 through activates TLR1 and TLR2 then stimulates the NF-kappa B activation to trigger the downstream cytokines, such as TNF-alpha and secreted alkaline phosphatase (SEAP). (C) 2019 Elsevier Masson SAS. All rights reserved.
• Pocket-based Lead Optimization Strategy for the Design and Synthesis of Chitinase Inhibitors
  作者：Yawen Dong、Song Hu、Xi Jiang、Tian Liu、Yun Ling、Xiongkui He、Qing Yang、Li Zhang

  DOI：10.1021/acs.jafc.9b00837

  日期：2019.4.3

  Insect chitinases play an indispensable role in shedding old cuticle during molting. Targeting chitinase inhibition is a promising pest control strategy. Of ChtI, a chitinase from the destructive insect pest Ostrinia furnacalis (Asian corn borer), has been suggested as a potential target for designing green pesticides. A 4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate scaffold was previously obtained, and further derivatization generated the lead compound 1 as Of ChtI inhibitor. Here, based on the predicted binding mode of compound 1, the pocket-based lead optimization strategy was applied. A series of analogues was synthesized, and their inhibitory activities against Of ChtI were evaluated. Compound 8 with 6-tert-pentyl showed preferential inhibitory activity with a Ki value of 0.71 mu M. Their structureactivity relationships suggested that the compound with larger steric hindrance at the 6-nonpolar group was essential for inhibitory activity due to its stronger interactions with surrounding amino acids. This work provides a strategy for designing potential chitinase inhibitors.
• Design, Synthesis, and Structure–Activity Relationship of <i>N</i>-Aryl-<i>N</i>′-(thiophen-2-yl)thiourea Derivatives as Novel and Specific Human TLR1/2 Agonists for Potential Cancer Immunotherapy
  作者：Zhipeng Chen、Lina Zhang、Junjie Yang、Lu Zheng、Fanjie Hu、Siqin Duan、Kutty Selva Nandakumar、Shuwen Liu、Hang Yin、Kui Cheng

  DOI：10.1021/acs.jmedchem.0c02266

  日期：2021.6.10

  cells. To the best of our knowledge, it is the first species-specific TLR1/2 agonist reported until now. Moreover, SMU-C80 increased the percentage of T, B, and NK cells ex vivo and activated the immune cells, which suppressed cancer cell growth in vitro. In summary, we obtained a highly efficient and specific human TLR1/2 agonist that acts through the MyD88 and NF-κB pathway, facilitating cytokine release

  之前对 1000 万种化合物的虚拟筛选产生了两种新的非脂肽样化学型作为 TLR2 激动剂。在此，我们介绍了我们最初命中的 1-苯基-3-(噻吩-2-基) 脲的化学优化，这导致将 SMU-C80 (EC 50 = 31.02 ± 1.01 nM)鉴定为 TLR2 特异性生物活性提高 370 倍的激动剂。机理研究表明，SMU-C80 通过 TLR1/2 募集接头蛋白 MyD88 并触发 NF-κB 通路以从人类而非鼠类细胞中释放细胞因子，例如 TNF-α 和 IL-1β。据我们所知，它是迄今为止报道的第一个物种特异性 TLR1/2 激动剂。此外，SMU-C80 增加了离体T、B 和 NK 细胞的百分比并激活免疫细胞，从而抑制体外癌细胞的生长。总之，我们获得了一种高效且特异的人 TLR1/2 激动剂，它通过 MyD88 和 NF-κB 途径起作用，促进细胞因子的释放和免疫细胞的同时激活，进而影响癌细胞的凋亡。
• [EN] ANTHELMINTIC AND INSECTICIDAL THIOPHENE DERIVATIVES<br/>[FR] VERMIFUGES ET INSECTICIDES A BASE DE DERIVES THIOPHENIQUES
  申请人：UPJOHN CO

  公开号：WO2003101979A1

  公开（公告）日：2003-12-11

  Novel anthelmintic compositions containing thiophene derivatives as active ingredients are disclosed.

  新的含有噻吩衍生物作为活性成分的驱虫剂组合物被揭示。