5-Chlor-2-chloracetylamino-benzthiazol | 3174-13-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: 5-Chlor-2-chloracetylamino-benzthiazol
• 英文别名: N-(6-chlorobenzothiazol-2-yl)-2-chloroacetamide；2-chloro-N-(5-chloro-benzothiazol-2-yl)-acetamide；2-chloro-N-(5-chloro-1,3-benzothiazol-2-yl)acetamide
• CAS: 3174-13-8
• 化学式: C₉H₆Cl₂N₂OS
• 分子量: 261.131
• InChiKey: QWUYZEYUMRSODV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  70.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-Chlor-2-chloracetylamino-benzthiazol 、 N,N-二甲基-对苯二胺 生成 N-(5-chloro-1,3-benzothiazol-2-yl)-2-[4-(dimethylamino)anilino]acetamide
  参考文献：
  名称：

  UPADHYAYA J. S., INDIAN J. PHARM. SCI., 1980, 42, NO 5, 133-135

  摘要：

  DOI：
• 作为产物：
  描述：

  2,5-二氯苯酚 以 乙醇 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 5-Chlor-2-chloracetylamino-benzthiazol
  参考文献：
  名称：

  Design of a delivery vehicle chitosan-based self-assembling: controlled release, high hydrophobicity, and safe treatment of plant fungal diseases

  摘要：

  Background Traditional pesticides are poorly water-soluble and suffer from low bioavailability. N-succinyl chitosan (NSCS) is a water-soluble chitosan derivative, has been recently used to encapsulate hydrophobic drugs to improve their bioavailability. However, it remains challenging to synthesize pesticides of a wide variety of water-soluble drugs and to scale up the production in a continuous manner. Results A synthetic method for preparing water-soluble nanopesticides with a polymer carrier was applied. The bioactive molecule BTL-11 was loaded into hollow NSCS to promote drug delivery, improve solubility and anti-fungal activity. The synthesized nanopesticides had well controlled sizes of 606 nm and the encapsulation rate was 80%. The release kinetics, drug toxicity and drug activity were further evaluated. The inhibitory activity of nanopesticides against Rhizoctonia solani (R. solani) was tested in vivo and in vitro. In vivo against R. solani trials revealed that BTL-11 has excellent control efficiency for cultivated rice leaf and sheath was 79.6 and 76.5%, respectively. By contrast, for BTL-11@NSCS NPs, the anti-fungal ability was strongly released and afforded significant control efficiencies of 85.9 and 81.1%. Those effects were significantly better than that of the agricultural fungicide azoxystrobin (51.5 and 66.5%). The proposed mechanism was validated by successfully predicting the synthesis outcomes. Conclusions This study demonstrates that NSCS is a promising biocompatible carrier, which can enhance the efficacy of pesticides, synergistically improve plant disease resistance, protect crop growth, and can be used for the delivery of more insoluble pesticides. Graphical Abstract

  DOI：

  10.1186/s12951-024-02386-8

文献信息

• Synthesis and anticonvulsant evaluation of indoline derivatives of functionalized aryloxadiazole amine and benzothiazole acetamide
  作者：Rajarshi Nath、M. Shahar Yar、Shelly Pathania、Gourav Grover、Biplab Debnath、Md Jawaid Akhtar

  DOI：10.1016/j.molstruc.2020.129742

  日期：2021.3

  structural requirement of pharmacophore and evaluated for anticonvulsant activities using maximal electroshock test (MES), subcutaneous pentylenetetrazole (scPTZ) seizures and neurotoxicity by motor impairment model in mice. The most active compoundN-(5-chlorobenzo[d]thiazol-2-yl)-2-(2,3-dioxoindolin-1-yl)acetamide (4a) has shown significant anticonvulsant activity against both MES and scPTZ screens

  摘要 一系列N-(取代苯并噻唑-2-基)-2-(2,3-二氧吲哚-1-基)乙酰胺(4a-i)和取代-[3-((5-苯基-1,3, 4-oxadiazole-2-yl)imino)indolene-2-one] (5a-f) 的设计、合成满足药效团的结构要求，并使用最大电击试验 (MES)、皮下戊四唑 (scPTZ) 癫痫发作评估抗惊厥活性小鼠运动损伤模型的神经毒性。最活跃的化合物 N-(5-chlorobenzo[d]thiazol-2-yl)-2-(2,3-dioxoindolin-1-yl)acetamide (4a) 对 MES 和 scPTZ 屏幕显示出显着的抗惊厥活性，并作为发现中位剂量为 35.7 mg/kg (MES ED50)、88.15 mg/kg (scPTZ ED50) 和毒性剂量 (TD50) 的最有效抗惊厥化合物 > 500 mg/kg。进行了包括分子对接研究在内的计算机模拟研究，以建立有效化合物
• Synthesis, antimicrobial activity, electrochemical studies and molecular modeling studies of novel 1,3,4-oxadiazole derivatives
  作者：Amal A. AL-Sharabi、Sana Saffour、Asaf Evrim Evren、Gizem Bayazıt、Gülşah Çongur、Ülküye Dudu Gül、Leyla Yurttaş

  DOI：10.1016/j.molstruc.2023.135775

  日期：2023.10

  recent decades has made the development of novel antimicrobial medications one of the medicinal chemists' top priorities. In this study, synthesis, in vitro antimicrobial activity, electrochemical studies, in silico pharmacokinetic ADME parameters, molecular docking, and molecular dynamic simulations were all performed on several 1,3,4-oxadiazole derivatives. The minimum inhibitory concentrations (MIC)

  近几十年来，抗菌素耐药 (AMR) 感染的高发率使得开发新型抗菌药物成为药物化学家的首要任务之一。在这项研究中，对几种 1,3,4-恶二唑衍生物进行了合成、体外抗菌活性、电化学研究、计算机药代动力学 ADME 参数、分子对接和分子动力学模拟。使用阿奇霉素作为参考抗菌剂，伏立康唑和氟康唑作为参考抗真菌剂，评估了这些化合物对 11 种革兰氏阳性菌、革兰氏阴性菌和真菌病原体的最低抑菌浓度 (MIC)。化合物4d 和 4f发现分别与阿奇霉素对粪肠球菌和大肠杆菌的效果大致相同，而三种化合物对近圆锥体显示出抗真菌活性，其 MIC 值与4g和4i的氟康唑以及4j的伏立康唑相同。此外，使用电化学技术评估了最有效的衍生物-双链 DNA (dsDNA) 相互作用。发现化合物4d、4f和4i会破坏 dsDNA 的结构，但化合物4h不能与 dsDNA 结合。此外，化合物4f的构效关系（SAR）和4d由分子模型研究阐明。
• Synthesis, Characterization and Biological Evaluation of Benzothiazole–Isoquinoline Derivative
  作者：Weihua Liu、Donghai Zhao、Zhiwen He、Yiming Hu、Yuxia Zhu、Lingjian Zhang、Lianhai Jin、Liping Guan、Sihong Wang

  DOI：10.3390/molecules27249062

  日期：——

  Currently, no suitable clinical drugs are available for patients with neurodegenerative diseases complicated by depression. Based on a fusion technique to create effective multi-target-directed ligands (MTDLs), we synthesized a series of (R)-N-(benzo[d]thiazol-2-yl)-2-(1-phenyl-3,4-dihydroisoquinolin-2(1H)-yl) acetamides with substituted benzothiazoles and (S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline

  目前，尚无适用于神经退行性疾病并发抑郁症患者的临床药物。基于创建有效的多目标定向配体 (MTDL) 的融合技术，我们合成了一系列 (R)-N-(benzo[d]thiazol-2-yl)-2-(1-phenyl-3, 4-dihydroisoquinolin-2(1H)-yl) acetamides with subSTituted benzothiazoles and (S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline. 通过体外酶活性测定测试所有化合物对单胺氧化酶 (MAO) 和胆碱酯酶 (ChE) 的抑制效力，并进一步测试其对单胺氧化酶 B (MAO-B) 和丁酰胆碱酯酶 (BuChE) 的特异性抑制效力。其中，6 种化合物（4b-4d、4f、4g 和 4i）表现出优异的活性。经典的抗抑郁药强迫游泳试验（FST）用于验证体外结果，表明六种化合物显着缩短了固定时间，尤其是化合物
• Sharma, Pratibha; Mandloi, Anupam; Pritmani, Shreeya, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1999, vol. 38, # 11, p. 1289 - 1294
  作者：Sharma, Pratibha、Mandloi, Anupam、Pritmani, Shreeya

  DOI：——

  日期：——
• Chaurasia; Sharma; Arora, Farmaco, Edizione Scientifica, 1982, vol. 37, # 3, p. 205 - 212
  作者：Chaurasia、Sharma、Arora

  DOI：——

  日期：——