Citation: Meena Kalawati, Kumari Sudesh, M. Khurana Jitender, Malik Amita, Sharma Chetan, Panwar Harsh. One pot three component synthesis of spiro[indolo-3, 10'-indeno[1, 2-b] quinolin]-2, 4, 11'-triones as a new class of antifungal and antimicrobial agents[J]. Chinese Chemical Letters, ;2017, 28(1): 136-142. doi: 10.1016/j.cclet.2016.06.025 shu

One pot three component synthesis of spiro[indolo-3, 10'-indeno[1, 2-b] quinolin]-2, 4, 11'-triones as a new class of antifungal and antimicrobial agents

Figures(7)

  • A simple and efficient three component procedure has been developed for the synthesis of highly substituted spiro[indolo-3, 10'-indeno[1, 2-b]quinolin]-2, 4, 11'-triones by one pot three component condensation of enaminones, isatin and indane-1, 3-dione in ethanol:water (1:1) in presence of ceric ammonium nitrate (CAN) as catalyst. This method provides several advantages such as lesser reaction time, high yield of products and operational simplicity. The antimicrobial activity of some of the compounds has been investigated against six microbial strains, some of the tested compounds showed good antimicrobial activity.
  • 加载中
    1. [1]

      Grare M., Mourer M., Fontanay S.. In vitro activity of para-guanidinoethylcalix[4] arene against susceptible and antibiotic-resistant Gram-negative and Gram-positive bacteria.[J]. J. Antimicrob. Chemother., 2007(60):575-581.  

    2. [2]

      (a) K.C. Joshi, A. Dandia, S. Baweja, A. Joshi, Studies in spiroheterocycles. Part XVâ…¡. Synthesis of novel fluorine containing spiro[indole-pyranobenzopyran] and spiro[indenopyran-indole] derivatives, J. Heterocycl. Chem. 26(1989) 1097-1099;
      (b) G. Jones, W.J. Rae, Knoevenagel condensation products from some cyclic ketones:structure and stereochemistry, Tetrahedron 22(1966) 3021-3026.

    3. [3]

      (a) A.H. Abdel-Rahman, E.M. Keshk, M.A. Hanna, S.M. El-Bady, Synthesis and evaluation of some new spiro indoline-based heterocycles as potentially active antimicrobial agents, Bioorg. Med. Chem. 12(2004) 2483-2488;
      (b) A. Dandia, R. Singh, S. Khaturia, et al., Efficient microwave enhanced regioselective synthesis of a series of benzimidazolyl/triazolyl spiro[indole-thiazolidinones] as potent antifungal agents and crystal structure of spiro[3H-indole-3, 2'-thiazolidine]-3'(1, 2, 4-triazol-3-yl)-2, 4'(1H)-dione, Bioorg. Med. Chem. 14(2006) 2409-2417.

    4. [4]

      Glover V., Halket J.M., Watkins P.J.. Isatin:identity with the purified endogenous monoamine oxidase inhibitor tribulin.[J]. J. Neurochem., 1998(51):656-659.  

    5. [5]

      Kumar R., Bansal R.C., Mahmood A.. Isatin, an inhibitor of acetylcholinesterase activity in rat brain.[J]. Biog. Amines, 1993,9:281-289.

    6. [6]

      A.E. Medvedev, A. Clow, M. Sandler, V. Glover, Isatin:a link between natriuretic peptides and monoamines? Biochem. Pharmacol. 52(1996) 385-391.

    7. [7]

      (a) S.K. Bhattacharya, V. Glover, I. McIntyre, G. Oxenkrug, M. Sandler, Stress causes an increase in endogenous monoamine oxidase inhibitor (tribulin) in rat brain, Neurosci. Lett. 92(1988) 218-221;
      (b) S.K. Bhattacharya, S.K. Mitra, S.B. Acharya, Anxiogenic activity of isatin, a putative biological factor, in rodents, J. Psychopharmacol. 5(1991) 202-206.

    8. [8]

      Rotstein B.H., Zaretsky S., Rai V., Yudin A.K.. Small heterocycles in multicomponent reactions.[J]. Chem. Rev., 2014,114:8323-8359. doi: 10.1021/cr400615v

    9. [9]

      (a) Y.O. Teng, H.Y. Zhao, J. Wang, et al., Synthesis and anti-cancer activity evaluation of 5-(2-carboxyethenyl)-isatin derivatives, Eur. J. Med. Chem. 112(2016) 145-156;
      (b) X.M. Zhang, H. Guo, Z.S. Li, et al., Synthesis and evaluation of isatin-β-thiosemicarbazones as novel agents against antibiotic-resistant Gram-positive bacterial species, Eur. J. Med. Chem. 101(2015) 419-430;
      (c) P. Sharma, K.R. Senwar, M.K. Jeengar, et al., H2O-mediated isatin spiro-epoxide ring opening with NaCN:synthesis of novel 3-tetrazolylmethyl-3-hydroxy-oxindole hybrids and their anticancer evaluation, Eur. J. Med. Chem. 104(2015) 11-24.

    10. [10]

      Mondal A., Brown M., Mukhopadhyay C.. Multicomponent, one-pot and expeditious synthesis of highly substituted new spiro[indolo-3, 10'-indeno[1, 2-b]quinolin]-2, 4, 11'-triones under micellar catalytic effect of CTAB in water.[J]. RSC Adv., 2014,4:36890-36895. doi: 10.1039/C4RA04918G

    11. [11]

      Kumari S., Rajeswari M., Khurana J.M.. La (OTf)3-catalyzed, three-component synthesis of spiro[Indolo-3, 10'-indeno[1, 2-b]quinolin]-2, 4, 11'-triones in PEG-400 under conventional heating and ultrasonic irradiation.[J]. Synth. Commun., 2016,46:387-394. doi: 10.1080/00397911.2016.1141427

    12. [12]

      (a) G. Khanna, K. Aggarwal, J.M. Khurana, An efficient and confluent approach for the synthesis of novel 3, 4-dihydro-2H-naphtho[2, 3-e][1, 3] oxazine-5, 10-dione derivatives by a three component reaction in ionic liquid, RSC Adv. 5(2015) 46448-46454;
      (b) P. Saluja, J.M. Khurana, C. Sharma, K.R. Aneja, An efficient and convenient approach for the synthesis of novel pyrazolo[12-a]triazole-triones and evaluation of their antimicrobial activities, Aust. J. Chem. 67(2014) 867-874;
      (c) H. Singh, J. Sindhu, J.M. Khurana, C. Sharma, K.R. Aneja, Ultrasound promoted one pot synthesis of novel fluorescent triazolyl spirocyclic oxindoles using DBU based task specific ionic liquids and their antimicrobial activity, Eur. J. Med. Chem. 77(2014) 145-154;
      (d) M. Rajeswari, P. Saluja, J.M. Khurana, A facile and green approach for the synthesis of spiro[naphthalene-2, 50-pyrimidine]-4-carbonitrile via a one-pot three-component condensation reaction using DBU as a catalyst, RSC Adv. 6(2016) 1307-1312;
      (e) M. Rajeswari, J. Sindhu, H. Singh, J.M. Khurana, An efficient, green synthesis of novel regioselective and stereoselective indan-1, 3-dione grafted spirooxindolopyrrolizidine linked 1, 2, 3-triazoles via a one-pot five-component condensation using PEG-400, RSC Adv. 5(2015) 39686-39691.

    13. [13]

      (a) C. Tietcheu, C. Garcia, D. Gardette, D. Dugat, J.C. Gramain, Efficient photochemical synthesis of tricyclic keto-indoles, J. Heterocycl. Chem. 39(2002) 965-973;
      (b) U.S. Sorensen, P. Villar, E. Helv, Synthesis of cyclopenta[b]indol-1-ones and carbazol-4-ones from N-(2-halophenyl)-substituted enaminones by intramolecular Heck reaction, Helvet. Chim. Acta 87(2004) 82-89;
      (c) F. Epifano, S. Genovese, M. Curini, Ytterbium triflate catalyzed synthesis of β-enaminones, Tetrahedron Lett. 48(2007) 2717-2720.

    14. [14]

      K.R. Aneja, C. Sharma, R. Joshi, In vitro efficacy of amaltas (Cassia fistula L.) against the pathogens causing otitis externa, J. Microbiol. 4(2011) 175-183.

  • 加载中
    1. [1]

      Ruike HuKangmin WangJunxiang LiuJingxian ZhangGuoliang YangLiqiu WanBijin Li . Extended π-conjugated systems by external ligand-assisted C−H olefination of heterocycles: Facile access to single-molecular white-light-emitting and NIR fluorescence materials. Chinese Chemical Letters, 2025, 36(4): 110113-. doi: 10.1016/j.cclet.2024.110113

    2. [2]

      Chong-Yang ShiJian-Xing GongZhen LiChao ShuLong-Wu YeQing SunBo ZhouXin-Qi Zhu . Gold-catalyzed intermolecular amination of allyl azides with ynamides: Efficient construction of 3-azabicyclo[3.1.0] scaffold. Chinese Chemical Letters, 2025, 36(2): 109895-. doi: 10.1016/j.cclet.2024.109895

    3. [3]

      Yinuo Wang Siran Wang Yilong Zhao Dazhen Xu . Selective Synthesis of Diarylmethyl Anilines and Triarylmethanes via Multicomponent Reactions: Introduce a Comprehensive Experiment of Organic Chemistry. University Chemistry, 2024, 39(8): 324-330. doi: 10.3866/PKU.DXHX202401063

    4. [4]

      Guangyao WangZhitong XuYe QiYueguang FangGuiling NingJunwei Ye . Electrospun nanofibrous membranes with antimicrobial activity for air filtration. Chinese Chemical Letters, 2024, 35(10): 109503-. doi: 10.1016/j.cclet.2024.109503

    5. [5]

      Uttam Pandurang Patil . Porous carbon catalysis in sustainable synthesis of functional heterocycles: An overview. Chinese Chemical Letters, 2024, 35(8): 109472-. doi: 10.1016/j.cclet.2023.109472

    6. [6]

      Wei-Tao DouQing-Wen ZengYan KangHaidong JiaYulian NiuJinglong WangLin Xu . Construction and application of multicomponent fluorescent droplets. Chinese Chemical Letters, 2025, 36(1): 109995-. doi: 10.1016/j.cclet.2024.109995

    7. [7]

      Zixu XiePengfei ZhangZiyao ZhangChen ChenXing Wang . The choice of antimicrobial polymers: Hydrophilic or hydrophobic?. Chinese Chemical Letters, 2024, 35(9): 109768-. doi: 10.1016/j.cclet.2024.109768

    8. [8]

      Mei PengWei-Min He . Photochemical synthesis and group transfer reactions of azoxy compounds. Chinese Chemical Letters, 2024, 35(8): 109899-. doi: 10.1016/j.cclet.2024.109899

    9. [9]

      Shehla KhalidMuhammad BilalNasir RasoolMuhammad Imran . Photochemical reactions as synthetic tool for pharmaceutical industries. Chinese Chemical Letters, 2024, 35(9): 109498-. doi: 10.1016/j.cclet.2024.109498

    10. [10]

      Kongchuan WuDandan LuJianbin LinTing-Bin WenWei HaoKai TanHui-Jun Zhang . Elucidating ligand effects in rhodium(Ⅲ)-catalyzed arene–alkene coupling reactions. Chinese Chemical Letters, 2024, 35(5): 108906-. doi: 10.1016/j.cclet.2023.108906

    11. [11]

      Shengkai LiYuqin ZouChen ChenShuangyin WangZhao-Qing Liu . Defect engineered electrocatalysts for C–N coupling reactions toward urea synthesis. Chinese Chemical Letters, 2024, 35(8): 109147-. doi: 10.1016/j.cclet.2023.109147

    12. [12]

      Ying-Di HaoZhi-Qian LinXiao-Yu GuoJiao LiangCan-Kun LuoQian-Tao WangLi GuoYong Wu . Rhodium-catalyzed Doyle-Kirmse rearrangement reactions of sulfoxoniun ylides. Chinese Chemical Letters, 2024, 35(4): 108834-. doi: 10.1016/j.cclet.2023.108834

    13. [13]

      Xiaoxue LiHongwei ZhouRongrong QianXu ZhangLei Yu . A concise synthesis of Se/Fe materials for catalytic oxidation reactions of anthracene and polyene. Chinese Chemical Letters, 2025, 36(3): 110036-. doi: 10.1016/j.cclet.2024.110036

    14. [14]

      Yi LuoLin Dong . Multicomponent remote C(sp2)-H bond addition by Ru catalysis: An efficient access to the alkylarylation of 2H-imidazoles. Chinese Chemical Letters, 2024, 35(10): 109648-. doi: 10.1016/j.cclet.2024.109648

    15. [15]

      Rong-Nan YiWei-Min He . Photocatalytic Minisci-type multicomponent reaction for the synthesis of 1-(halo)alkyl-3-heteroaryl bicyclo[1.1.1]pentanes. Chinese Chemical Letters, 2024, 35(10): 110115-. doi: 10.1016/j.cclet.2024.110115

    16. [16]

      Hong ZhangCui-Ping LiLi-Li WangZhuo-Da ZhouWen-Sen LiLing-Yi KongMing-Hua Yang . Asperochones A and B, two antimicrobial aromatic polyketides from the endophytic fungus Aspergillus sp. MMC-2. Chinese Chemical Letters, 2024, 35(9): 109351-. doi: 10.1016/j.cclet.2023.109351

    17. [17]

      Yaxian LiangQingyi LiLiwei HuRuohan ZhaiFan LiuLin TanXiaofei WangHuixu Xie . Environmentally friendly polylysine gauze dressing for an innovative antimicrobial approach to infected wound management. Chinese Chemical Letters, 2024, 35(10): 109459-. doi: 10.1016/j.cclet.2023.109459

    18. [18]

      Hao SunShengke LiQian LiuMinzan ZuoXueqi TianKaiya WangXiao-Yu Hu . Supramolecular prodrug vesicles for selective antimicrobial therapy employing a chemo-photodynamic strategy. Chinese Chemical Letters, 2025, 36(3): 109999-. doi: 10.1016/j.cclet.2024.109999

    19. [19]

      Yunfen GaoLiying WangChufan ZhouYi ZhaoHai HuangJun Wu . Low-dimensional antimicrobial nanomaterials in anti-infection treatment and wound healing. Chinese Chemical Letters, 2025, 36(3): 110028-. doi: 10.1016/j.cclet.2024.110028

    20. [20]

      Chunru Liu Ligang Feng . Advances in anode catalysts of methanol-assisted water-splitting reactions for hydrogen generation. Chinese Journal of Structural Chemistry, 2023, 42(10): 100136-100136. doi: 10.1016/j.cjsc.2023.100136

Metrics
  • PDF Downloads(4)
  • Abstract views(884)
  • HTML views(76)

通讯作者: 陈斌, bchen63@163.com
  • 1. 

    沈阳化工大学材料科学与工程学院 沈阳 110142

  1. 本站搜索
  2. 百度学术搜索
  3. 万方数据库搜索
  4. CNKI搜索
Address:Zhongguancun North First Street 2,100190 Beijing, PR China Tel: +86-010-82449177-888
Powered By info@rhhz.net

/

DownLoad:  Full-Size Img  PowerPoint
Return