Synthesis and Antitumor Activity of Novel 4H-1,2,4-Benzothiadiazine 1,1-Dioxide Derivatives

doi:10.11944/j.issn.1000-0518.2016.09.150420

Chinese Journal of Applied Chemistry ›› 2016, Vol. 33 ›› Issue (9): 1067-1072.DOI: 10.11944/j.issn.1000-0518.2016.09.150420

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Synthesis and Antitumor Activity of Novel 4H-1,2,4-Benzothiadiazine 1,1-Dioxide Derivatives

TAN Xuxia^a,LI Shining^a,ZHAO Jie^b,MAO Shen^a,MAO Longfei^a,XU Guiqing^a^*()

^aSchool of Chemistry and Chemical Engineering,He'nan Normal university,Xinxiang,He'nan 453007,China
^bTopfond Pharmaceutical Limited by Share Ltd,Zhumadian,He'nan 463000,China

Received:2015-11-30 Accepted:2016-03-24 Published:2016-08-23 Online:2016-08-23
Contact: XU Guiqing
Supported by:
Supported by the National Natural Science Foundation of China(No.21402043), the Industry, University, Research Project of He'nan(No.132107000035)

Abstract

Abstract:

Twelve unreported 4H-1,2,4-benzothiadiazine 1,1-dioxide derivatives were synthesized from 2-nitrobenzene sulfonyl chloride with good water-solubility in high yields. These compounds were characterized by ¹H NMR, ¹³C NMR, MS-ESI and elemental analysis. Their inhibiting effects on HepG-2 cell were evaluated with MTT protocol. The results show that 7-(aminomethyl)-3-cyclopropyl-1,1-dioxide-4H-benzo[e][1,2,4]thiadiazine(7c) exhibits the highest inhibition rate of 79.3% among the synthesized compounds.

Key words: 4H-benzothiadiazine dioxides derivatives, synthesis, antitumor activities

TAN Xuxia, LI Shining, ZHAO Jie, MAO Shen, MAO Longfei, XU Guiqing. Synthesis and Antitumor Activity of Novel 4H-1,2,4-Benzothiadiazine 1,1-Dioxide Derivatives[J]. Chinese Journal of Applied Chemistry, 2016, 33(9): 1067-1072.

References

[1]	Boverie S,Antoine M H,Somers F,et al.Effect on KATP channel Activation Properties and Tissue Selectivity of the Nature of the Substituent in the 7- and the 3-Position of 4H-1,2,4-Benzothiadiazine 1,1-Dioxides[J]. J Med Chem,2005,48(10):3492-3503.
[2]	Pirotte B,Antoine M H,Hermann M,et al.A Pyridothiadiazine(BPDZ44) as a New and Potent Activator of ATP- Sensitive K+ Channels[J]. Biochem Pharmacol,1994,47(8):1381-1386.
[3]	Tullio P,Pirotte B,Lebrun P,et al.3- and 4-Substituted 4H-Pyrido[4,3-e]-1,2,4-Thiadiazine 1,1-Dioxides as Potassium Channel Openers:Synthesis, Pharmacological Evaluation and Structure Activity Relationships[J]. J Med Chem,1996,39(4):937-948.
[4]	Boverie S,Antoine M H,Tullio P,et al.Effect on Insulin Release of Compounds Structurally Related to the Potassium Channel Opener 7-Chloro-3-Isopropylamino-4H-1,2,4-Benzothiadiazine 1,1-Dioxide(BPDZ73):Introduction of Heteroatoms on the 3-Alkyl-Amino Side Chain of the Benzothiadiazine 1,1-Dioxide ring[J]. J Pharm Pharmacol,2001,53(7):973-980.
[5]	Lebrun P,Arkhammar P,Antoine M H,et al.A Potent Diazoxide Analogue Activating ATP- Sensitive K+ Channels and Inhibiting Insulin Release[J]. Diabetologia,2000,43(6):723-732.
[6]	Cook N S,Quast U. Potassium Channel Pharmacology. In Potassium Channels, Structure, Classification, Function and Therapeutic Potential[M]. U.K:Ellis Horwood Press,1990,181-225.
[7]	Goerke J,Liu N,Sarisky R T,et al.Substituted Benzothiadizine Inhibitors of Hepatitis C Virus Polymerase[J]. Bioorg Med Chem Lett,2009,19(15):4350-4353.
[8]	Merck S,Dohme C. N-Piperidin-4-yl Derivatives:English, WO2013/041457 A1[P].2013-03-28.
[9]	Tullio P,Pirotte B,Somers F,et al.Study of the Ring Closure Reaction of O-Aminoaryl-Sulfonamides with 1,1-Thiocarbonyldiimidazole[J]. Tetrahedron,1998,54(19):4935-4942.
[10]	Nielsen F E,Bodvarsdottir T B,Worsaae A,et al.6-Chloro-3-Alkylamino-4H-Thieno[3,2-e]-1,2,4-Benzothiadiazine 1,1-Dioxide Dderivatives Potently and Selectively Activate ATP Sensitive Potassium Channels of Pancreatic B-cells[J]. J Med Chem,2002,45(19):4171-4187.
[11]	Novello F C,Bell S C, Abram s E L A ,et al. Diuretics:1,2,4-Benzothiadiazine-1,1-Dioxides[J]. J Org Chem,1960,25(6):970-981.
[12]	Yale H L,Losee K,Bernstein J. 6-(Trifluoromethyl)-1,2,4-Benzothiadiazine-7-Sulfonamide-1,1-Dioxide and Related Compounds[J]. J Am Chem Soc,1960,82(8):2042-2046.
[13]	Miecznikowska-Stolarczyk W. Carboxyazobenzenesulfonamides and Their N-Halo Derivatives.Ⅱ.The Condensation of Nitrobenzenesulfonamides and Aaminobenzoic Acids[J]. Lodz Towarz Nauk Wydzial Ⅲ, Acta Chim,1962,8:95-104.
[14]	Schrader E. Hydrazides and Azides of Sulfocarboxylic Acids.Ⅱ.Rearrangement of o-Aminosulfonylbenzoyl Azide[J]. J Chem Soc,Abstr,1918,114(1):1-49.
[15]	Chen X,Zhu C J,Guo F,et al.Acetic Acid Derivatives of 3,4-Dihydro-2H-1,2,4-benzothiadiazine 1,1-Dioxide as a Novel Class of Potent Aldose Reductase Inhibitors[J]. J Med Chem,2010,53(23):8330-8334.
[16]	YANG Lei,FAN Lianghua,ZHAO Dandan,et al.Synthesis and Antiproliferative Activity of 22-Abeo-Stigmast-22-Nitrogen-Containing Compounds[J]. Chinese J Appl Chem,2015,32(3):273-277(in Chinese). 杨雷,范良华,赵丹丹,等. 22-降-豆甾-22-含氮化合物的合成及抗肿瘤活性[J]. 应用化学,2015,32(3):273-277.
[17]	ZHANG Fuxing,KUANG Daizhi,FENG Yonglan,et al.Synthesis, Structure and Antitum Activities of Tri(o-bromobenzyl)tin Dithiotetrahydropyrrolocarbamate[J]. Chinese J Appl Chem,2014,31(3):285-289(in Chinese). 张复兴,邝代治,冯泳兰,等. 锡吡咯烷基二硫代甲酸酯的合成、结构及体外抗癌活性[J]. 应用化学,2014,31(3):285-289.
[18]	GUAN Songlei,HU Xiuli,LIU Zhongying,et al.Anti-tumor Effect of Curcumin Combining with Cis-Platin on Human Ovrian Cancer Cell Line COC1 in Vitro[J]. Chinese J Appl Chem,2011,28(9):1022-1027(in Chinese). 关松磊,胡秀丽,刘忠英,等. 姜黄素联合顺铂对卵巢癌细胞COC1的体外抗肿瘤作用[J]. 应用化学,2011,28(9):1022-1027.

Synthesis and Antitumor Activity of Novel 4H-1,2,4-Benzothiadiazine 1,1-Dioxide Derivatives

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