6-溴-2-(2-噻吩)-4-喹啉羧酸 | 33289-49-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 中文名称: 6-溴-2-(2-噻吩)-4-喹啉羧酸
• 中文别名: 6-溴-2-噻吩-2-基喹啉-4-羧酸
• 英文名称: 6-bromo-2-(thiophen-2-yl)quinoline-4-carboxylic acid
• 英文别名: 6-bromo-2-[2]thienyl-quinoline-4-carboxylic acid；6-Brom-2-[2]thienyl-chinolin-4-carbonsaeure；6-Bromo-2-thien-2-ylquinoline-4-carboxylic acid；6-bromo-2-thiophen-2-ylquinoline-4-carboxylic acid
• CAS: 33289-49-5
• 化学式: C₁₄H₈BrNO₂S
• mdl: MFCD00178255
• 分子量: 334.193
• InChiKey: KYHKYEUYJZTRCP-UHFFFAOYSA-N

物化性质

• 溶解度：
  >50.1 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  78.4
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  6-溴-2-(2-噻吩)-4-喹啉羧酸 在 硫酸 、 硝酸 作用下， 反应 1.0h， 以68%的产率得到6-Bromo-2-(3,5-dinitro-thiophen-2-yl)-quinoline-4-carboxylic acid
  参考文献：
  名称：

  一些喹啉衍生物的合成和药理性质。

  摘要：

  一系列2-（2-噻吩基）辛二酸3，其衍生物5和4-（3-取代的1,2,4-三唑并[3,4-b] -1,3,4-噻二唑-6-合成了yl）-2-（2-噻吩基）喹啉6。新合成的化合物的结构通过分析，IR，NMR和质谱数据确定。评价新合成的化合物的抗炎，镇痛和驱虫活性。结果表明，二硝基噻吩衍生物5具有更高的活性。

  DOI：

  10.1016/s0014-827x(98)00037-8
• 作为产物：
  描述：

  5-溴靛红 生成 6-溴-2-(2-噻吩)-4-喹啉羧酸
  参考文献：
  名称：

  TRAXTENBERG, P. L.;ZEMTSOVA, M. N.;MOISEEV, I. K.;SIDOROVA, N. V., IX BCEC. SIMP. PO TSELENAPRAVL. IZYSKANIYU LEKARSTV. VESHCHESTV, YURMALA,+

  摘要：

  DOI：

文献信息

• Design and Synthesis of Some 1,3,4-Thiadiazole Amines: Molecular Docking, in silico ADMET, in vitro Antimicrobials and Antioxidant Studies
  作者：Sakshith Raghavendra Prasad、Nayak Devappa Satyanarayan、Avarse Satish Kumar Shetty、Harishkumar Shivanna、Basaiah Thippeswamy

  DOI：10.14233/ajchem.2022.23760

  日期：——

  An increase in free radical concentration in the human body due to medications leads to oxidative stress can be counteracted by novel antioxidative agents that lower the concentration of free radical and free radical damages in human body. In present study, 2-thiophene 4-thiadiazole quinoline derivatives (5a-e) were designed and synthesized using 2-thiophene quinoline 4-carboxylic acids and thiosemicarbazide. The designed compounds 5a-e were docked against the protein PDB-ID: 1OC3 and evaluated the antioxidant activity using DPPH assay and also screened for antibacterial and antifungal potential by Agar well diffusion assay followed by in vitro antitubercular assay by MABA method. The IC50 values for compounds 5a and 5b were 415 μg/mL and 396 μg/mL. The binding affinity of docked ligands against the protein 1OC3 ranges from -6.2 to -5.7 kcal/mol. In an antimicrobial investigation, the compounds were found to be active against both bacteria and fungi, as well as sensitive to M. tuberculosis.

  由于药物导致人体自由基浓度增加，导致氧化应激，可以通过新型抗氧化剂降低人体内自由基和自由基损伤的浓度来对抗。在本研究中，使用2-噻吩喹啉-4-羧酸和硫脲制备了2-噻吩-4-噻二唑喹啉衍生物（5a-e）。将设计的化合物5a-e与蛋白质PDB-ID：1OC3进行对接，并使用DPPH法评估其抗氧化活性，然后通过琼脂扩散法筛选其抗菌和抗真菌潜力，并通过MABA法进行体外抗结核试验。化合物5a和5b的IC50值分别为415 μg/mL和396 μg/mL。对接配体与蛋白质1OC3的结合亲和力范围为-6.2至-5.7 kcal/mol。在抗微生物调查中，发现这些化合物对细菌和真菌都有活性，并且对结核分枝杆菌敏感。
• Unveiling the crystal structure and quantum properties of 6‑bromo-N-pyridin-4-yl-2-thiophen-2-ylquinoline-4-carboxamide: A promising journey towards predicting its anticancer potential
  作者：T.S. Shashidhara、C.S. Navyashree、M.K. Hema、K. Mantelingu、R. Jothi Ramalingam、Muthusamy Karnan、M. Umashankar、N.K. Lokanath

  DOI：10.1016/j.molstruc.2023.136266

  日期：2023.12

  The wide range of pharmalogical activity exhibited by quinoline derivatives, due to its fused benzene ring with pyridine structure, has made them a popular framework for medicinal chemistry. The single crystal X-ray diffraction and quantum computational studies revealed the crystal packing of the novel saturated quinoline derivative, 6‑bromo-N-pyridin-4-yl-2-thiophen-2-ylquinoline-4-carboxamide. The

  喹啉衍生物由于其稠合苯环与吡啶结构而表现出广泛的药理活性，使其成为药物化学的流行框架。单晶 X 射线衍射和量子计算研究揭示了新型饱和喹啉衍生物 6-溴-N-吡啶-4-基-2-噻吩-2-基喹啉-4-甲酰胺的晶体堆积。标题分子的结构检查揭示了羧基官能团和 N-杂环吡啶环参与各种分子间相互作用，这些相互作用负责维持晶体稳定性，这一点通过赫什菲尔德表面分析得到了验证。此外，在计算机模拟中进行了研究以仔细检查标题分子的抗致癌特性。拓扑异构酶是一种参与 DNA 复制和修复的重要酶，可调节 DNA 局部结构，使其成为靶向抗癌疗法的主要候选者。通过分子对接确定配体与目标蛋白可接受的结合亲和力，并进行动态模拟，在100ns的模拟周期内监测和分析配体-蛋白复合物的波动。最终，新分子在目标蛋白的底物结合口袋内表现出最有利的相互作用和稳定性。
• The Pfitzinger Reaction in the Synthesis of Quinoline Derivatives
  作者：Ng. Ph. Buu-Hoi、R. Royer、Ng. D. Xuong、P. Jacquignon

  DOI：10.1021/jo50015a019

  日期：1953.9
• Heterocyclic Diamidine DNA Ligands as HOXA9 Transcription Factor Inhibitors: Design, Molecular Evaluation, and Cellular Consequences in a HOXA9-Dependant Leukemia Cell Model
  作者：Sabine Depauw、Mélanie Lambert、Samy Jambon、Ananya Paul、Paul Peixoto、Raja Nhili、Laura Marongiu、Martin Figeac、Christelle Dassi、Charles Paul-Constant、Benjamin Billoré、Arvind Kumar、Abdelbasset A. Farahat、Mohamed A. Ismail、Ekaterina Mineva、Daniel P. Sweat、Chad E. Stephens、David W. Boykin、W. David Wilson、Marie-Hélène David-Cordonnier

  DOI：10.1021/acs.jmedchem.8b01448

  日期：2019.2.14

  Most transcription factors were for a long time considered as undruggable targets because of the absence of binding pockets for direct targeting. HOXA9, implicated in acute myeloid leukemia, is one of them. To date, only indirect targeting of HOXA9 expression or multitarget HOX/PBX protein/protein interaction inhibitors has been developed. As an attractive alternative by inhibiting the DNA binding, we selected a series of heterocyclic diamidines as efficient competitors for the HOXA9/DNA interaction through binding as minor groove DNA ligands on the HOXA9 cognate sequence. Selected DB818 and DB1055 compounds altered HOXA9-mediated transcription in luciferase assays, cell survival, and cell cycle, but increased cell death and granulocyte/monocyte differentiation, two main HOXA9 functions also highlighted using transcriptomic analysis of DB818-treated murine Hoxa9-transformed hematopoietic cells. Altogether, these data demonstrate for the first time the propensity of sequence-selective DNA ligands to inhibit HOXA9/DNA binding both in vitro and in a murine Hoxa9-dependent leukemic cell model.
• 2(5-Nitro-2-thienyl)cinchoninic acids
  作者：Iradj Lalezari、F. Ghabgharan、R. Maghsoudi

  DOI：10.1021/jm00287a031

  日期：1971.5