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1141998388

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1¡¢Synthesis and Antibacterial Evaluation of New Sulfone Derivatives Containing 2-Aroxymethyl-1,3,4-Oxadiazole/Thiadiazole Moiety£¬Molecules 2017, 22(1), 64¡£
2¡¢Cinchona Alkaloid Derivative-Catalyzed Enantioselective Synthesis via a Mannich-Type Reaction and Antifungal Activity of ¦Â-Amino Esters Bearing Benzoheterocycle Moieties. [J]. Molecules. 2014. 19: 3955-3972.

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Synthesis and Antibacterial Evaluation of New Sulfone Derivatives Containing 2-Aroxymethyl-1,3,4-Oxadiazole/Thiadiazole Moiety

×÷Õß:Su, SH (Su, Shihu)[ 1,2 ] ; Zhou, X (Zhou, Xia)[ 1 ] ; Liao, GP (Liao, Guoping)[ 1 ] ; Qi, PY (Qi, Puying)[ 1 ] ; Jin, LH (Jin, Linhong)[ 1 ]

MOLECULES

¾í: 22

ÆÚ: 1

ÎÄÏ׺Å: 64

DOI: 10.3390/molecules22010064

³ö°æÄê: JAN 2017

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Sulfones are one of the most important classes of agricultural fungicides. To discover new lead compounds with high antibacterial activity, a series of new sulfone derivatives were designed and synthesized by introducing the aroxymethyl moiety into the scaffold of 1,3,4-oxadiazole/thiadiazole sulfones. Antibacterial activities against three phytopathogens (Xanthomonas oryzae pv. oryzae, Ralstonia solanacearum, Xanthomonas axonopodis pv. citri.) were assayed in vitro. As compared to the control of commercial fungicides and some reported sulfone fungicides, seven compounds 5I-1-5I-7 exerted remarkably higher activities with EC50 values ranging from 0.45-1.86 mu g/mL against X. oryzae and 1.97-20.15 mu g/mL against R. solanacearum. Exhilaratingly, 5I-1, 5I-2 and 5I-4 displayed significant in vivo activity against X. oryzae with protective effect of 90.4%, 77.7%, and 81.1% at 200 mu g/mL, respectively, much higher than that exhibited by Bismerthiazol (25.6%) and Thiadiazole-copper (32.0%). And the differential phytotoxicity of active derivatives was preliminarily checked. The results demonstrated that derivative of 2-aroxymethyl-1,3,4-oxadiazole/thiadiazole sulfone can serve as potential alternative bactericides for the management of plant bacterial diseases.
¹Ø¼ü´Ê

×÷Õ߹ؼü´Ê:synthesis; 1,3,4-oxadiazole/thiadiazole sulfone; aryloxymethyl; antibacterial activity; structure-activity relationship

KeyWords Plus:ANTIFUNGAL ACTIVITY; BACTERIAL WILT; INHIBITORS; ORYZAE; BLIGHT
×÷ÕßÐÅÏ¢

ͨѶ×÷ÕßµØÖ·: Zhou, X; Jin, LH (ͨѶ×÷Õß)
[ÏÔʾÔöÇ¿×éÖ¯ÐÅÏ¢µÄÃû³Æ]         Guizhou Univ, Res & Dev Ctr Fine Chem, State Key Lab Breeding Base Green Pesticide & Agr, Key Lab Green Pesticide & Agr Bioengn,Minist Educ, Guiyang 550025, Peoples R China.

µØÖ·:
[ÏÔʾÔöÇ¿×éÖ¯ÐÅÏ¢µÄÃû³Æ]         [ 1 ] Guizhou Univ, Res & Dev Ctr Fine Chem, State Key Lab Breeding Base Green Pesticide & Agr, Key Lab Green Pesticide & Agr Bioengn,Minist Educ, Guiyang 550025, Peoples R China
              [ 2 ] Zunyi Agr Prod Qual & Safety Inspect & Testing Ct, Room 698,Shanghai Rd, Zunyi 563000, Guizhou, Peoples R China

µç×ÓÓʼþµØÖ·:happytt365@foxmail.com; zhouxia_j@126.com; lgp899017@163.com; qpuying000@163.com; linhong_j@126.com
»ù½ð×ÊÖúÖÂл
»ù½ð×ÊÖú»ú¹¹        ÊÚȨºÅ
National Natural Science Foundation of China        
20962005
Excellent Young Science and Technology Talent Cultivation Plan        
201122
²é¿´»ù½ð×ÊÖúÐÅÏ¢   
³ö°æÉÌ

MDPI AG, ST ALBAN-ANLAGE 66, CH-4052 BASEL, SWITZERLAND
Àà±ð / ·ÖÀà

Ñо¿·½Ïò:Chemistry

Web of Science Àà±ð:Chemistry, Organic
ÎÄÏ×ÐÅÏ¢

ÎÄÏ×ÀàÐÍ:Article

ÓïÖÖ:English

Èë²ØºÅ: WOS:000395473500064

ISSN: 1420-3049
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    Impact Factor (Ó°ÏìÒò×Ó): Journal Citation Reports

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IDS ºÅ: EM7EE

Web of Science ºËÐĺϼ¯ÖÐµÄ "ÒýÓõIJο¼ÎÄÏ×": 28

Web of Science ºËÐĺϼ¯ÖÐµÄ "±»ÒýƵ´Î": 0
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1141998388: ½ð±Ò+100, ¡ïÓаïÖú, ÓÐûÓÐWord»òPDF¸ñʽ£¬ÓÃÀ´ÆÀÖ°³ÆµÄ£¬Ð»Ð» 2017-08-02 15:02:46
sunshan4379: Ó¦ÖúÖ¸Êý-1, ÇëÎðÓ¦ÖúÎ¥¹æÌû£¬Ð»Ð»ºÏ×÷£¡ 2017-08-04 14:36:19
Cinchona Alkaloid Derivative-Catalyzed Enantioselective Synthesis via a Mannich-Type Reaction and Antifungal Activity of beta-Amino Esters Bearing Benzoheterocycle Moieties

×÷Õß:Xiao, H (Xiao, Han)[ 1,2 ] ; Wu, F (Wu, Fang)[ 1 ] ; Shi, L (Shi, Li)[ 1 ] ; Chen, ZW (Chen, Zhiwei)[ 1 ] ; Su, SH (Su, Shihu)[ 1 ] ; Tang, CH (Tang, Chenghao)[ 1 ] ; Wang, HT (Wang, Hongtao)[ 1 ] ; Li, ZN (Li, Zhining)[ 1 ] ; Li, MC (Li, Meichuan)[ 1 ] ; Shi, QC (Shi, Qingcai)[ 1 ]

MOLECULES

¾í: 19

ÆÚ: 4

Ò³: 3955-3972

DOI: 10.3390/molecules19043955

³ö°æÄê: APR 2014

²é¿´ÆÚ¿¯Ó°Ïì
ÕªÒª

An efficient synthesis of highly functionalized chiral beta-amino ester derivatives containing benzothiophene and benzothiazole moieties is developed by a Mannich-type reaction using a cinchona alkaloid-derived thiourea catalyst. The desired products were obtained in good yields and high enantioselectivities (similar to 86% yield, >99% ee) using to the optimized reaction conditions. The synthesized compounds were characterized by H-1-NMR, C-13-NMR, IR, and HREI-MS analyses. The bioassays identified that compound 5dr has excellent antifungal activity, with a 60.53% inhibition rate against F. oxysporum, higher than that of the commercial agricultural fungicide hymexazol, whose inhibition rate was 56.12%.
¹Ø¼ü´Ê

×÷Õ߹ؼü´Ê:beta-amino acid ester; antifungal activity; benzoheterocycle; enantioselective synthesis

KeyWords Plus:ASYMMETRIC STRECKER REACTION; AZA-HENRY REACTION; STEREOSELECTIVE-SYNTHESIS; CHIRAL CATALYSTS; ACYL IMINES; ACID-ESTER; PART 1; 1,3-DICARBONYLS; ANTIBACTERIAL; INHIBITORS
×÷ÕßÐÅÏ¢

ͨѶ×÷ÕßµØÖ·: Xiao, H (ͨѶ×÷Õß)
[ÏÔʾÔöÇ¿×éÖ¯ÐÅÏ¢µÄÃû³Æ]         Guizhou Univ, Key Lab Green Pesticide & Agr Bioengn, Minist Educ, Guiyang 550025, Peoples R China.

µØÖ·:
[ÏÔʾÔöÇ¿×éÖ¯ÐÅÏ¢µÄÃû³Æ]         [ 1 ] Guizhou Univ, Key Lab Green Pesticide & Agr Bioengn, Minist Educ, Guiyang 550025, Peoples R China
[ÏÔʾÔöÇ¿×éÖ¯ÐÅÏ¢µÄÃû³Æ]         [ 2 ] Guizhou Minzu Univ, Sch Chem & Environm Sci, Guiyang 550025, Peoples R China

µç×ÓÓʼþµØÖ·:hanx@gzmu.edu.cn; fangwu90@163.com; s2012l@sina.com; yan.zhilie@163.com; sushihu999@gmail.com; chtang1122@163.com; wanghongtao1115@126.com; aning072@126.com; lmcuvhn1987@163.com; shiqingcai1988@163.com
»ù½ð×ÊÖúÖÂл
»ù½ð×ÊÖú»ú¹¹        ÊÚȨºÅ
National Natural Science Foundation of China        
2132003
20872021
Science and Technology Foundation of Guizhou province        
20092058
²é¿´»ù½ð×ÊÖúÐÅÏ¢   
³ö°æÉÌ

MDPI AG, POSTFACH, CH-4005 BASEL, SWITZERLAND
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Ñо¿·½Ïò:Chemistry

Web of Science Àà±ð:Chemistry, Organic
ÎÄÏ×ÐÅÏ¢

ÎÄÏ×ÀàÐÍ:Article

ÓïÖÖ:English

Èë²ØºÅ: WOS:000336087800008

PubMed ID: 24694652

ISSN: 1420-3049
ÆÚ¿¯ÐÅÏ¢

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    Impact Factor (Ó°ÏìÒò×Ó): Journal Citation Reports

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IDS ºÅ: AH4HK

Web of Science ºËÐĺϼ¯ÖÐµÄ "ÒýÓõIJο¼ÎÄÏ×": 52

Web of Science ºËÐĺϼ¯ÖÐµÄ "±»ÒýƵ´Î": 3
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