Citation: Hemalatha Gadegoni, Sarangapani Manda. Synthesis and screening of some novel substituted indoles contained 1,3,4-oxadiazole and 1,2,4-triazole moiety[J]. Chinese Chemical Letters, ;2013, 24(2): 127-130. shu

Synthesis and screening of some novel substituted indoles contained 1,3,4-oxadiazole and 1,2,4-triazole moiety

Hemalatha Gadegoni ^a,, ,
Sarangapani Manda ^b

1.
a Jayamukhi College of Pharmacy, Narsampet, Warangal 506332, India;
2.
b University College of Pharmaceutical Sciences, Kakatiya University, Warangal 506009, India

Corresponding author: Hemalatha Gadegoni,
Received Date: 21 August 2012
Available Online: 20 December 2012

A series of novel 3-[5-(1H-indol-3-yl-methyl)-2-oxo-[1,3,4]oxadiazol-3-yl]propionitrile (5), 3-[4-amino-3-(1H-indol-3-yl-methyl)-5-oxo-4,5-dihydro-[1,2,4]triazol-1-yl]propionitrile (6), 3-[5-(1H-indol-3-yl-methyl)-2-thioxo-[1,3,4]oxadiazol-3-yl]propionitrile (7) and 3-[4-amino-3-(1H-indol-3-ylmethyl)-5-thioxo-4,5-dihydro-[1,2,4]triazol-1-yl]propionitrile (8) were synthesized in good yields from the intermediate (1H-indol-3-yl)-acetic acid N'-(2-cyanoethyl)hydrazide (4). The chemical structures of the newly synthesized compounds were elucidated by their IR, ¹H NMR and MS. Further, all the compounds were screened for their antimicrobial activity against Gram-positive, Gram-negative bacteria and also tested their ability toward anti-inflammatory activity.
- 1,3,4-Oxadiazols,
- 1,2,4-Triazols,
- Antimicrobial activity,
- Anti-inflammatory
1. [1]
  [1] C.C. Paraschivescu, F. Dumitrascu, C. Draghici, et al., New non-symmetrical 2,5-disubstituted 1,3,4-oxadiazoles bearing a benzo[b]-thiophene moiety, Arkivoc (2008) 198-206.
2. [2]
  [2] M.P. Hutt, E.F. Elstager, L.M. Werbet, 2-Phenyl-5-(trichloromethyl)-1,3,4-oxadiazoles: a newclass of anti-malarial substances, J.Heterocycl. Chem. 7 (1970) 511-581.
3. [3]
  [3] F. Omar, N. Mahfouz, M. Rahman, Design, synthesis and antiinflammatory activity of some 1,3,4-oxadiazole derivatives, Eur. J. Med. Chem. 31 (1996) 819-825.
4. [4]
  [4] M. Zareef, R. Iqbal, N.G. De Dominguez, et al., Synthesis and antimalarial activity of novel chiral and achiral benzenesulfonamides bearing 1,3,4-oxadiazole moieties, J. Enzyme Inhib. Med. Chem. 22 (2007) 301-308.
5. [5]
  [5] A. Omar, M.E. Mohsen, O.M. Aboulwafa, Synthesis and anticonvulsant properties of a novel series of 2-substituted amino-5-aryl-1,3,4-oxadiazole derivatives, J. Heterocycl. Chem. 21 (1984) 1415-1418.
6. [6]
  [6] A. Husain, M. Ajmal, Synthesis of novel 1,3,4-oxadiazole derivatives and their biological properties, Acta Pharm. 59 (2009) 223-233.
7. [7]
  [7] S.L. Gaonkar, K.M. Rai, Synthesis and antimicrobial studies of a new series of 2-{4-[2-(5-ethylpyridin-2-yl)ethoxy]phen-yl}-5-substituted-1,3,4-oxadiazoles, Eur. J. Med. Chem. 41 (2006) 841-846.
8. [8]
  [8] M.A. Ali, M.S. Yar, Oxadiazole mannich bases: synthesis and antimycobacterial activity, Bioorg. Med. Chem. Lett. 17 (2007) 3314-3316.
9. [9]
  [9] A. Zarghi, S.A. Tabatabai, M. Faizi, et al., Synthesis and anticonvulsant activity of new 2-substituted-5-(2-benzyloxyphenyl)-1,3,4-oxadiazoles, Bioorg. Med. Chem. Lett. 15 (2005) 1863-1865.
10. [10]
  [10] Z.H. Luo, S.Y. He, B.Q. Chen, et al., Synthesis and in vitro antitumor activity of 1,3,4-oxadiazole derivatives based on benzisoselenazolone, Chem. Pharm. Bull. 60 (2012) 887-891.
11. [11]
  [11] V.J. Ram, H.N. Pandey, Synthesis and anti-inflammatory activity of benzal-3-pentadecylaryloxyalkyl carboxylic acid hydrazides and 2-benzalamino-5-(3'-pentadecylaryloxyalkyl)-1,3,4-oxadiazo-les, Eur. J. Med. Chem. 25 (1990) 541-548.
12. [12]
  [12] P.J. Shirote, M.S. Bhatia, Synthesis, characterization and antiinflammatory activity of 5-{[((5-substituted-aryl)-1,3,4-thiadiazol-2-yl)thio]-n-alkyl}-1,3,4-oxadiazole-2-thiol, Chin. J. Chem. 28 (2010) 1429-1436.
13. [13]
  [13] V. Padmavathi, G.S. Reddy, A. Padmaja, P. Kondaiah, Ali-Shazia, Synthesis, antimicrobial and cytotoxic activities of 1,3,4-oxadiazoles, 1,3,4-thiadiazoles and 1,2,4-triazoles, Eur. J. Med. Chem. 44 (2009) 2106-2112.
14. [14]
  [14] B. Jayashankar, K.M.L. Rai, N. Baskaran, H.S.S. Shazia, Synthesis and pharmacological evaluation of 1,3,4-oxadiazole bearing bis(heterocycle) derivatives as antiinflammatory and analgesic agents, Eur. J. Med. Chem. 44 (2009) 3898-3902.
15. [15]
  [15] F.A. Omar, N.M. Mahfouz, M.A. Rahman, Design, synthesis and antiinflammatory activity of some 1,3,4-oxadiazole derivatives, Eur. J. Med. Chem. 31 (1996) 819-825.
16. [16]
  [16] N.D. Heindel, J.R. Reid, Synthesis and anticonvulsant properties of a novel series of 2-substituted amino-5-aryl-1,3,4-oxadiazole derivatives, J. Heterocycl. Chem. 17 (1980) 1087-1088.
17. [17]
  [17] J. Haber, Present status and perspectives on antimycoties with systematic effects, Cas. Lek. Cesk. 140 (2001) 596-604.
18. [18]
  [18] S.C. Benner, V.B. Jigajiani, V.V. Badiyer, Pyrimidines VI, synthesis of 2-methyl thio-5-bromo pyrimidine-4-carboxylic acid thiosemicarbazides, 3-pyrimidy-1,2,4(H)-triazole and 2-aryl amino-1,3,4-thiadiazole, Rev. Roum. Chim. 21 (1976) 757.
19. [19]
  [19] M. Nakanishi, T. Tahara, K. Araki, et al., Synthesis and structure-activity relations of 5-phenyl-1, 3-dihydro-2H-thieno[2,3][1,4]diazepin-2-ones, J. Med. Chem. 16 (1973) 214-219.
20. [20]
  [20] R.M. Shaker, The chemistry of mercapto and thione substituted 1,2,4-triazoles and their utility in heterocyclic synthesis, Arkivoc (2006) 59-112.
21. [21]
  [21] H.A. Burch, W.O. Smith, Nitrofuryl heterocycles. Ⅲ. 3-Alkyl-5-(5-nitro-2-furyl)-1,2,4-triazoles and intermediates, J. Med. Chem. 9 (1966) 405-408.
22. [22]
  [22] M.G. Mamolo, D. Zampieri, V. Falagiani, et al., Antifungal and antimycobacterial activity of new N1-[1-aryl-2-(1H-imidazol-1-yl and 1H-1,2,4-triazol-1-yl)-ethylidene]-pyridine-2-carboxami-drazone derivatives: a combined experimental and computational approach, Arkivoc (2004) 231-250.
23. [23]
  [23] I. Mir, M.T. Siddiqui, A. Comrie, Antituberculosis agents I: a-[5-(2-furyl)-1, 2,4-triazol-3-ylthio]acethydrazide and related compounds, Tetrahedron 26 (1970) 5235-5238.
24. [24]
  [24] B.S. Holla, B. Veerendra, M.K. Shivananda, B. Poojary, Synthesis characterization and anticancer activity studies on some mannich bases derived from 1,2,4-triazoles, Eur. J. Med. Chem. 38 (2003) 759-767.
25. [25]
  [25] H.L. Yale, J.J. Piala, Substituted s-triazoles and related compounds, J. Med. Chem. 9 (1966) 42-46.
26. [26]
  [26] M.Y. Mhasalkar, M.H. Shah, S.T. Nikam, K.G.A. Narayanan, C.V. Deliwala, 4-Alkyl-5-aryl-4H-1,2,4-triazole-3-thiols as hypoglycemic agents, J. Med. Chem. 13 (1970) 672-674.
27. [27]
  [27] C.A. Winter, E.A. Risley, G.N. Nus, Carrageenin-induced edema in hind paw of the rat as an assay for antiinflammatory drugs, Proc. Soc. Exp. Biol. Med. 111 (1962) 544-547.
1. [1]
  Xiongbo Song , Jinwen Xiao , Juan Wu , Li Sun , Long Chen . Decellularized amniotic membrane promotes the anti-inflammatory response of macrophages via PI3K/AKT/HIF-1α pathway. Chinese Chemical Letters, 2025, 36(1): 109844-. doi: 10.1016/j.cclet.2024.109844
2. [2]
  Chunhua Ma , Mengjiao Liu , Siyu Ouyang , Zhenwei Cui , Jingjing Bi , Yuqin Jiang , Zhiguo Zhang . Metal-free construction of diverse 1,2,4-triazolo[1,5-a]pyridines on water. Chinese Chemical Letters, 2025, 36(1): 109755-. doi: 10.1016/j.cclet.2024.109755
3. [3]
  Guangyao Wang , Zhitong Xu , Ye Qi , Yueguang Fang , Guiling Ning , Junwei Ye . Electrospun nanofibrous membranes with antimicrobial activity for air filtration. Chinese Chemical Letters, 2024, 35(10): 109503-. doi: 10.1016/j.cclet.2024.109503
4. [4]
  Xiaoyao Ma , Jinling Zhang , Ge Fang , He Gao , Jie Gao , Li Fu , Yuanyuan Hou , Gang Bai . Förster resonance energy transfer reveals phillygenin and swertiamarin concurrently target AKT on different binding domains to increase the anti-inflammatory effect. Chinese Chemical Letters, 2024, 35(5): 108823-. doi: 10.1016/j.cclet.2023.108823
5. [5]
  Wenjia Wang , Xingyue He , Xiaojie Wang , Tiantian Zhao , Osamu Muraoka , Genzoh Tanabe , Weijia Xie , Tianjiao Zhou , Lei Xing , Qingri Jin , Hulin Jiang . Glutathione-depleted cyclodextrin pseudo-polyrotaxane nanoparticles for anti-inflammatory oxaliplatin (Ⅳ) prodrug delivery and enhanced colorectal cancer therapy. Chinese Chemical Letters, 2024, 35(4): 108656-. doi: 10.1016/j.cclet.2023.108656
6. [6]
  Shiqi Xu , Zi Ye , Shuang Shang , Fengge Wang , Huan Zhang , Lianguo Chen , Hao Lin , Chen Chen , Fang Hua , Chong-Jing Zhang . Pairs of thiol-substituted 1,2,4-triazole-based isomeric covalent inhibitors with tunable reactivity and selectivity. Chinese Chemical Letters, 2024, 35(7): 109034-. doi: 10.1016/j.cclet.2023.109034
7. [7]
  Tianlong Zhang , Rongling Zhang , Hongsheng Tang , Yan Li , Hua Li . Online Monitoring and Mechanistic Analysis of 3,5-diamino-1,2,4-triazole (DAT) Synthesis via Raman Spectroscopy: A Recommendation for a Comprehensive Instrumental Analysis Experiment. University Chemistry, 2024, 39(6): 303-311. doi: 10.3866/PKU.DXHX202312006
8. [8]
  Yulong Shi , Fenbei Chen , Mengyuan Wu , Xin Zhang , Runze Meng , Kun Wang , Yan Wang , Yuheng Mei , Qionglu Duan , Yinghong Li , Rongmei Gao , Yuhuan Li , Hongbin Deng , Jiandong Jiang , Yanxiang Wang , Danqing Song . Chemical construction and anti-HCoV-OC43 evaluation of novel 10,12-disubstituted aloperine derivatives as dual cofactor inhibitors of TMPRSS2 and SR-B1. Chinese Chemical Letters, 2024, 35(5): 108792-. doi: 10.1016/j.cclet.2023.108792
9. [9]
  Hong Zhang , Cui-Ping Li , Li-Li Wang , Zhuo-Da Zhou , Wen-Sen Li , Ling-Yi Kong , Ming-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
10. [10]
  Junjun Huang , Ran Chen , Yajian Huang , Hang Zhang , Anran Zheng , Qing Xiao , Dan Wu , Ruxia Duan , Zhi Zhou , Fei He , Wei Yi . Discovery of an enantiopure N-[2-hydroxy-3-phenyl piperazine propyl]-aromatic carboxamide derivative as highly selective α_1D/1A-adrenoceptor antagonist and homology modelling. Chinese Chemical Letters, 2024, 35(11): 109594-. doi: 10.1016/j.cclet.2024.109594
11. [11]
  Cailiang Yue , Nan Sun , Yixing Qiu , Linlin Zhu , Zhiling Du , Fuqiang Liu . A direct Z-scheme 0D α-Fe₂O₃/TiO₂ heterojunction for enhanced photo-Fenton activity with low H₂O₂ consumption. Chinese Chemical Letters, 2024, 35(12): 109698-. doi: 10.1016/j.cclet.2024.109698
12. [12]
  Yuanyuan Zeng , Fang Liu , Jun Wang , Bianfei Shao , Tao He , Zhongzheng Xiang , Yan Wang , Shunyao Zhu , Tian Yang , Siting Yu , Changyang Gong , Lei Liu . Fisetin micelles precisely exhibit a radiosensitization effect by inhibiting PDGFRβ/STAT1/STAT3/Bcl-2 signaling pathway in tumor. Chinese Chemical Letters, 2025, 36(2): 109734-. doi: 10.1016/j.cclet.2024.109734
13. [13]
  Zixu Xie , Pengfei Zhang , Ziyao Zhang , Chen Chen , Xing Wang . The choice of antimicrobial polymers: Hydrophilic or hydrophobic?. Chinese Chemical Letters, 2024, 35(9): 109768-. doi: 10.1016/j.cclet.2024.109768
14. [14]
  Hai-Yang Song , Jun Jiang , Yu-Hang Song , Min-Hang Zhou , Chao Wu , Xiang Chen , Wei-Min He . Supporting-electrolyte-free electrochemical [2 + 2 + 1] annulation of benzo[d]isothiazole 1,1-dioxides, N-arylglycines and paraformaldehyde. Chinese Chemical Letters, 2024, 35(6): 109246-. doi: 10.1016/j.cclet.2023.109246
15. [15]
  Jinge Zhu , Ailing Tang , Leyi Tang , Peiqing Cong , Chao Li , Qing Guo , Zongtao Wang , Xiaoru Xu , Jiang Wu , Erjun Zhou . Chlorination of benzyl group on the terminal unit of A₂-A₁-D-A₁-A₂ type nonfullerene acceptor for high-voltage organic solar cells. Chinese Chemical Letters, 2025, 36(1): 110233-. doi: 10.1016/j.cclet.2024.110233
16. [16]
  Xuewei BA , Cheng CHENG , Huaikang ZHANG , Deqing ZHANG , Shuhua LI . Preparation and luminescent performance of Sr_1-xZrSi₂O₇∶xDy³⁺ phosphor with high thermal stability. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 357-364. doi: 10.11862/CJIC.20240096
17. [17]
  Peiyan Zhu , Yanyan Yang , Hui Li , Jinhua Wang , Shiqing Li . Rh(Ⅲ)‐Catalyzed sequential ring‐retentive/‐opening [4 + 2] annulations of 2H‐imidazoles towards full‐color emissive imidazo[5,1‐a]isoquinolinium salts and AIE‐active non‐symmetric 1,1′‐biisoquinolines. Chinese Chemical Letters, 2024, 35(10): 109533-. doi: 10.1016/j.cclet.2024.109533
18. [18]
  You Zhou , Li-Sheng Wang , Shuang-Gui Lei , Bo-Cheng Tang , Zhi-Cheng Yu , Xing Li , Yan-Dong Wu , Kai-Lu Zheng , An-Xin Wu . I₂-DMSO mediated tetra-functionalization of enaminones for the construction of novel furo[2′,3′:4,5]pyrimido[1,2-b]indazole skeletons via in situ capture of ketenimine cations. Chinese Chemical Letters, 2025, 36(1): 109799-. doi: 10.1016/j.cclet.2024.109799
19. [19]
  Xiangyuan Zhao , Jinjin Wang , Jinzhao Kang , Xiaomei Wang , Hong Yu , Cheng-Feng Du . Ni nanoparticles anchoring on vacuum treated Mo2TiC2Tx MXene for enhanced hydrogen evolution activity. Chinese Journal of Structural Chemistry, 2023, 42(10): 100159-100159. doi: 10.1016/j.cjsc.2023.100159
20. [20]
  Anqiu LIU , Long LIN , Dezhi ZHANG , Junyu LEI , Kefeng WANG , Wei ZHANG , Junpeng ZHUANG , Haijun HAO . Synthesis, structures, and catalytic activity of aluminum and zinc complexes chelated by 2-((2,6-dimethylphenyl)amino)ethanolate. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 791-798. doi: 10.11862/CJIC.20230424

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(698)
HTML views(33)

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