2-硝基-5-噻吩-2-基苯胺 | 849235-53-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-硝基-5-噻吩-2-基苯胺
• 英文名称: 2-nitro-5-(thiophen-2-yl)aniline
• 英文别名: 2-nitro-5-thiophen-2-yl-phenylamine；2-nitro-5-thiophen-2-ylaniline
• CAS: 849235-53-6
• 化学式: C₁₀H₈N₂O₂S
• 分子量: 220.252
• InChiKey: AVLRTOLFIYWLBH-UHFFFAOYSA-N

物化性质

• 沸点：
  418.3±35.0 °C(Predicted)
• 密度：
  1.391±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  100
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-硝基-5-噻吩-2-基苯胺 在 iron(III) chloride 、 一水合肼 作用下， 以 甲醇 为溶剂， 生成 4-(thiophen-2-yl)benzene-1,2-diamine
  参考文献：
  名称：

  Synthesis and antimicrobial activity of novel substituted 4-[3-(1H-benzimidazol-2-yl)-4-hydroxybenzyl]-2-(1H-benzimidazol-2-yl)phenol derivatives

  摘要：

  A series of novel substituted bis-benzimidazole derivatives were synthesized by reaction of 5,5'-methylenebis(2-hydroxybenzaldehyde) with various substituted o-phenylenediamines in glacial acetic acid. The structure of the newly synthesized compounds was elucidated by H-1 and C-13 NMR, FT-IR, and MS spectra, and their antimicrobial activity against gram positive and gram negative bacteria and antifungal activity were evaluated. The thienyl-substituted derivative showed significant activity against Bacillus licheniformis. Bacillus subtilis, Staphylococcus aureus, Klebsiella pneumonia (bacteria), and Fusarium solani (fungi). The activities of the fluoro-substituted substituted derivative against some bacterial strains and of the thienyl-substituted derivative against fungi were found to be similar to those of standard drugs.

  DOI：

  10.1134/s1070363217110202
• 作为产物：
  描述：

  2-噻吩硼酸 、 5-溴-2-硝基苯胺 在 四(三苯基膦)钯 potassium carbonate 、 三(邻甲基苯基)磷 作用下， 以 乙二醇二甲醚 、 水 为溶剂， 生成 2-硝基-5-噻吩-2-基苯胺
  参考文献：
  名称：

  具有增强的效能和选择性的新型氨基苯基苯甲酰胺型组蛋白脱乙酰基酶抑制剂。

  摘要：

  人们正在作出巨大的努力来了解HDAC同种型在人类癌症中的作用，并开发具有更好治疗窗的抗肿瘤药。这项工作的一部分是探索与酶催化位点相邻的14 A内部腔，这导致设计和合成具有不寻常的双（芳基）型药效团的化合物4。围绕该铅的SAR研究导致优化了有效的，选择性的，非异羟肟酸HDAC抑制剂。

  DOI：

  10.1021/jm701079h

文献信息

• [EN] INHIBITORS OF HISTONE DEACETYLASE<br/>[FR] INHIBITEURS D'HISTONE DEACETYLASE
  申请人：METHYLGENE INC

  公开号：WO2005030704A1

  公开（公告）日：2005-04-07

  The invention relates to the inhibition of histone deacetylase. The invention provides compounds and methods for inhibiting histone deacetylase enzymatic activity. The invention also provides compositions and methods for treating cell proliferative diseases and conditions.

  这项发明涉及抑制组蛋白去乙酰化酶。该发明提供了抑制组蛋白去乙酰化酶酶活性的化合物和方法。该发明还提供了治疗细胞增殖性疾病和症状的组合物和方法。
• Inhibitors of histone deacetylase
  申请人：The Broad Institute, Inc.

  公开号：US09365498B2

  公开（公告）日：2016-06-14

  The present invention relates to compounds of formula (I): or a pharmaceutically acceptable salt, hydrate, solvate, or prodrug thereof, wherein U, J, V, X, R2a, R2b, R2c, R5 and t are as described herein. The present invention relates generally to inhibitors of histone deacetylase and to methods of making and using them. These compounds are useful for promoting cognitive function and enhancing learning and memory formation. In addition, these compounds are useful for treating, alleviating, and/or preventing various conditions, including for example, neurological disorders, memory and cognitive function disorders/impairments, extinction learning disorders, fungal diseases and infections, inflammatory diseases, hematological diseases, and neoplastic diseases in humans and animals.

  本发明涉及以下式(I)的化合物： 或其药学上可接受的盐、水合物、溶剂合物或前药，其中U、J、V、X、R2a、R2b、R2c、R5和t如本文所述。本发明一般涉及组织脱乙酰酶抑制剂及其制备和使用方法。这些化合物对促进认知功能、增强学习和记忆形成有用。此外，这些化合物对治疗、缓解和/或预防各种疾病条件有用，例如神经系统疾病、记忆和认知功能障碍/损伤、消退学习障碍、真菌疾病和感染、炎症性疾病、血液病和人类及动物的肿瘤性疾病。
• Inhibitors of Histone Deacetylase
  申请人：Moradei Oscar

  公开号：US20080132459A1

  公开（公告）日：2008-06-05

  The invention relates to the inhibition of histone deacetylase. The invention provides compounds and methods for inhibiting histone deacetylase enzymatic activity. The invention also provides compositions and methods for treating cell proliferative diseases and conditions.

  本发明涉及抑制组蛋白去乙酰化酶的方法。本发明提供了抑制组蛋白去乙酰化酶酶活性的化合物和方法。本发明还提供了用于治疗细胞增殖性疾病和病状的组合物和方法。
• INHIBITORS OF HISTONE DEACETYLASE
  申请人：The Broad Institute, Inc.

  公开号：US20160251351A1

  公开（公告）日：2016-09-01

  The present invention relates to compounds of formula (I): or a pharmaceutically acceptable salt, hydrate, solvate, or prodrug thereof, wherein U, J, V, X, R 1a , R 2b , R 2c , R 5 and t are as described herein. The present invention relates generally to inhibitors of histone deacetylase and to methods of making and using them. These compounds are useful for promoting cognitive function and enhancing learning and memory formation. In addition, these compounds are useful for treating, alleviating, and/or preventing various conditions, including for example, neurological disorders, memory and cognitive function disorders/impairments, extinction learning disorders, fungal diseases and infections, inflammatory diseases, hematological diseases, and neoplastic diseases in humans and animals.

  本发明涉及化合物式(I)或其药学上可接受的盐、水合物、溶剂合物或前药，其中U、J、V、X、R1a、R2b、R2c、R5和t如本文所述。本发明通常涉及组织脱乙酰化酶抑制剂及其制备和使用方法。这些化合物有助于促进认知功能，增强学习和记忆形成。此外，这些化合物在治疗、缓解和/或预防各种疾病方面也很有用，包括例如神经系统疾病、记忆和认知功能障碍、消退学习障碍、真菌疾病和感染、炎症性疾病、血液疾病和动物的肿瘤性疾病。
• Anti-tumor activity of new orally bioavailable 2-amino-5-(thiophen-2-yl)benzamide-series histone deacetylase inhibitors, possessing an aqueous soluble functional group as a surface recognition domain
  作者：Yoshiyuki Hirata、Masahiko Hirata、Yasuyuki Kawaratani、Makio Shibano、Masahiko Taniguchi、Masahide Yasuda、Yoshiro Ohmomo、Yasuo Nagaoka、Kimiye Baba、Shinichi Uesato

  DOI：10.1016/j.bmcl.2012.01.053

  日期：2012.3

  New orally bioavailable 5-(thiophen-2-yl)-substituted 2-aminobenzamide-series histone deacetylase inhibitors were synthesized. These compounds possess a morpholine or piperadine-derived moiety as an aqueous soluble functional group. Among them, 8b, having a 4-ethyl-2,3-dioxopiperazine-1-carboxamide group as a surface recognition domain, showed promising inhibitory activities against HCT116 cell growth and HDAC1/2. Notably, unlike MS-275, this compound did not induce apoptosis in the cell cycle tests. We therefore conducted antitumor tests of 8b and MS-275 against HCT116 cell xenografts in nude mice. Compound 8b reduced the volume of tumor mass to T/C: 60% and 47% at 45 and 80 mg/kg over 16 days, respectively. These values were comparable to the rate (T/C: 51% at 45 mg/kg) for MS-275. Furthermore, 8b, at neither 45 nor 80 mg/kg, induced the weight loss which was observed in the mice given MS-275 at 45 mg/kg. (c) 2012 Elsevier Ltd. All rights reserved.