N-(benzo[d]thiazol-2-yl)-1-(3-nitrophenyl)methanimine | 69791-43-1

• 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: N-(benzo[d]thiazol-2-yl)-1-(3-nitrophenyl)methanimine
• 英文别名: benzothiazol-2-yl-(3-nitro-benzylidene)-amine；2-Benzothiazolamine, N-[(3-nitrophenyl)methylene]-；N-(1,3-benzothiazol-2-yl)-1-(3-nitrophenyl)methanimine
• CAS: 69791-43-1
• 化学式: C₁₄H₉N₃O₂S
• 分子量: 283.31
• InChiKey: BELDGJOBVUQMQA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 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：
  99.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-丁炔酸甲酯 、 N-(benzo[d]thiazol-2-yl)-1-(3-nitrophenyl)methanimine 在 copper(l) iodide 、 silica gel 作用下， 200.0 ℃ 、1.52 MPa 条件下， 反应 3.3h， 以60%的产率得到methyl [6-(3-nitrophenyl)imidazo[2,1-b][1,3]thiazol-5-yl]acetate
  参考文献：
  名称：

  分批连续流铜催化A 3偶联合成咪唑并[ 2,1 - b ]噻唑

  摘要：

  开发了一种简单的方法，在铜（I，II）催化下，从苯甲醛，2-氨基噻唑和炔烃开始合成官能化的咪唑并[ 2,1- b ]噻唑。该协议允许构建各种芳基取代的咪唑并[2,1- b ]苯并噻唑，-[2,1- b ]噻唑和-[2,1- b ] [1,3,4]噻二唑。反应易于进行，以33–93％的收率提供了大多数所需的产物。在连续流反应器中工艺的强化将产品的收率提高到定量。

  DOI：

  10.1021/acs.joc.7b01762
• 作为产物：
  描述：

  苯胺 在 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 N-(benzo[d]thiazol-2-yl)-1-(3-nitrophenyl)methanimine
  参考文献：
  名称：

  苯并噻唑类似物：合成，表征，使用PM6和DFT进行MO计算，计算机模拟研究以及作为DHFR抑制剂和抗菌活性的体外抗疟药

  摘要：

  苯并噻唑类似物因其抗疟疾和微生物感染的潜在活性而备受关注。为了寻找合适的抗微生物剂和抗疟疾剂，我们在这里报告了苯并噻唑类似物（J 1-J 10）的合成，表征和生物学活性。通过IR，质量，1 H NMR，13 C NMR和元素分析来表征分子。的体外抗微生物活性进行了研究抗致病性菌株; 通过DFT和PM6分子轨道计算对结果进行了解释。研究了该分子对粟酒裂殖酵母细胞的体外细胞毒性和遗传毒性。体外研究了抗疟活性。进一步评估了活性化合物J 1，J 2，J 3，J 5和J 6对受体Pf-DHFR的酶抑制作用，进行了计算和体外研究，以检查其作为二氢叶酸铅还原酶抑制剂的候选资格。

  DOI：

  10.1016/j.bmc.2017.07.057

文献信息

• Enantioselective Aza-Henry Reaction of Imines Bearing a Benzothiazole Moiety Catalyzed by a<i>Cinchona</i>-Based Squaramide
  作者：Hai-Xiao He、Wen Yang、Da-Ming Du

  DOI：10.1002/adsc.201200957

  日期：2013.4.15

  efficient enantioselective aza‐Henry reaction of nitroalkanes to imines bearing a benzothiazole moiety catalyzed by a Cinchona‐based squaramide has been developed. In the reaction of imines, the corresponding products were obtained in good to excellent yields (up to 99%) with excellent enantioselectivities (up to >99% ee) for most of the aromatic substituted imines. The imines with electron‐withdrawing groups

  已经开发了一种有效的对映选择性氮烷烃对氮苯-亨利反应，该反应由基于Cinchona的方酰胺催化的带有苯并噻唑部分的亚胺形成。在亚胺的反应中，对于大多数芳族取代的亚胺，以良好至优异的收率（高达99％）和优异的对映选择性（高达> 99％ee）获得了相应的产物。在氮杂-亨利反应中，具有吸电子基团的亚胺比带有供电子基团的亚胺具有更好的收率。此外，还开发了使用2-氨基苯并噻唑，醛和硝基甲烷的单锅三组分对映选择性氮杂-亨利反应。在单锅情况下获得了中等至良好的收率和高对映选择性（高达98％ee）。
• Chiral Phosphoric Acid‐Catalyzed Enantioselective Formal [4+2] Cycloaddition Between Dienecarbamates and 2‐Benzothioazolimines
  作者：Wei‐Yang Ma、Emeric Montinho‐Inacio、Bogdan I. Iorga、Pascal Retailleau、Xavier Moreau、Luc Neuville、Géraldine Masson

  DOI：10.1002/adsc.202200161

  日期：2022.5.17

  cycloaddition between 2-benzothiazolimines and N-H-1,3-dienecarbamates is described. A divergence in reaction pathways was observed depending on the dienes employed. The reaction performed with 4-substituted dienes produced benzothiazolopyrimidines as major product in yields ranging from 42 to 67%, as single diastereoisomer and with enantioselectivity between 93 and 99%. The same reaction performed with

  描述了 2-苯并噻唑亚胺和N -H-1,3-二烯氨基甲酸酯之间的对映选择性手性磷酸催化的形式 [4+2] 环加成。根据所使用的二烯，观察到反应途径的分歧。用 4-取代二烯进行的反应产生苯并噻唑并嘧啶作为主要产物，产率范围为 42% 至 67%，为单一非对映异构体，对映选择性在 93% 至 99% 之间。然而，用 3-取代二烯进行的相同反应得到高度对映体富集的 1,2,3,4-四氢喹啉作为主要产物，尽管具有中等的非对映选择性。
• Squaramide-catalysed enantionselective Mannich reaction of imines bearing a heterocycle with malonates
  作者：Hai-Xiao He、Da-Ming Du

  DOI：10.1039/c3ra43260b

  日期：——

  An efficient enantioselective Mannich reaction of imines bearing a heterocycle with malonates catalysed by a cinchona-based squaramide organocatalyst has been developed. This catalytic asymmetric reaction afforded the β-amino ester derivatives containing a heterocycle moiety in high yields (up to 99%) and excellent enantioselectivities (up to 98%) in most cases. The imines with an electron-withdrawing

  已经开发了一种有效的对映选择性曼尼奇反应，该亚胺带有一个由金鸡纳基方酸酰胺有机催化剂催化的丙二酸酯。该催化不对称反应在大多数情况下以高产率（高达99％）和优异的对映选择性（高达98％）提供了含有杂环部分的β-氨基酯衍生物。在该反应中，具有吸电子基团的亚胺比带有电子给体基团的亚胺具有更好的收率。
• Diastereo‐ and Enantioselective Mannich/Cyclization Cascade Reaction Access to Chiral Benzothiazolopyrimidine Derivatives
  作者：Yan Zhang、Jia‐Hui Yang、Ying‐Qi Xia、Lin Dong、Fen‐Er Chen

  DOI：10.1002/chem.202005509

  日期：2021.4.7

  An efficient asymmetric Mannich/cyclization cascade strategy was established from 2‐benzothiazolimines with N‐acylpyrazoles to provide optical active benzothiazolopyrimidine derivatives using a copper‐based complex. The mild cascade process constructed various structurally diverse products with broad scope of substrates together with excellent enantioselectivities (up to 99 % ee) and diastereoselectivities

  一种有效的不对称曼尼希/环化级联策略是从2-苯并噻唑啉与N-酰基吡唑建立的，以使用铜基络合物提供光学活性的苯并噻唑并嘧啶衍生物。温和的级联过程构建了各种结构多样的产品，具有广泛的底物范围，同时具有出色的对映选择性（高达99％ee）和非对映选择性（高达99：1 dr）。
• Synthesis and biological evaluation of benzo[d]isothiazole, benzothiazole and thiazole Schiff bases
  作者：Paola Vicini、Athina Geronikaki、Matteo Incerti、Bernadetta Busonera、Graziella Poni、Carla Alba Cabras、Paolo La Colla

  DOI：10.1016/s0968-0896(03)00493-0

  日期：2003.11

  Three new series of benzo[d]isothiazole, benzothiazole and thiazole Schiff bases were synthesized and tested in vitro with the aim of identifying novel lead compounds active against emergent and re-emergent human and cattle infectious diseases (AIDS, hepatitis B and C, tuberculosis. bovine viral diarrhoea) or against drug-resistant cancers (leukaemia, carcinoma, melanoma, MDR tumors) for which no definitive cure or efficacious vaccine is available at present. In particular, these compounds were evaluated in vitro against representatives of different virus classes, such as a HIV-1 (Retrovirus), a HBV (Hepadnavirus) and the single-stranded RNA(+) viruses Yellow fever virus (YFV) and Bovine viral diarrhoea virus (BVDV), both belonging to Flaviviridae. Title compounds were also tested against representatives of Gram-positive and Gram-negative bacteria (Staphylococcus aureus, Salmonella spp.), various atypic mycobacterial strains Mycobacterium fortuitom and Mycobacterium smegmatis), yeast (Candida albicans) and mould (Aspergillus fumigatus). None of the compounds showed antiviral or antimicrobial activity. The benzo[ci]isothiazole compounds showed a marked Cytotoxicity (CC50 = 4-9 muM) against the human CD4(+) lymphocytes (MT-4) that were used to support HIV-1 growth. For this reason, the most cytotoxic compounds of this series were evaluated for their antiproliferative activity against a panel of human cell lines derived from haematological and solid tumors. The results highlighted that all the benzo[d]isothiazole derivatives inhibited the growth of leukaemia cell lines, whereas only one of the above mentioned compounds (1e) showed antiproliferative activity against two solid tumor-derived cell lines. (C) 2003 Elsevier Ltd. All rights reserved.