Synthesis of Novel 3-(Piperazin-1-yl)-1,2-benzothiazole Derivatives and Their Antibacterial Activity

被引：3

作者：

Garlapati, Krishna Kanth ^{[1
]}

Srinivasu, N. ^{[1
]}

Kumar, K. Siva ^{[2
]}

Ganta, Ravi Kumar ^{[3
]}

机构：

[1] Vignans Fdn Sci Technol & Res, Dept Sci & Humanities, Div Chem, Vadlamudi 522213, Guntur, India

[2] GITAM Deemed Univ, Dept Biotechnol, GSS, Visakhapatnam 530045, India

[3] GITAM Deemed Univ, Dept Chem, GSS, Visakhapatnam 530045, India

来源：

RUSSIAN JOURNAL OF ORGANIC CHEMISTRY | 2022年 / 58卷 / 10期

关键词：

3-(piperazin-1-yl)-1; 2-benzothiazole derivatives; antibacterial activity; Lipinski's rule of five; drug likeness; agar diffusion method; BIS(HETEROARYL)PIPERAZINES; DISCOVERY;

D O I：

10.1134/S1070428022100220

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new library of structurally modified 3-(piperazin-1-yl)-1,2-benzothiazole derivatives have been designed and synthesized through a multi-step procedure. Their structures were characterized by IR, H-1 NMR, C-13 NMR, and mass spectral technique. The synthesized compounds were evaluated for drug likeness or "drugability " according to Lipinski's rule of five (RO5). One of the compounds showed two violations, whereas the others complied with RO5. The synthesized compounds were also screened for their antibacterial activity by the agar diffusion method, and three of them were found to be active. One of the compounds showed a good activity against Bacillus subtilis and Staphylococcus aureus with MIC 500 mu g/mL. The compound with RO5 violations exhibited almost no antibacterial activity.

引用

页码：1534 / 1541

页数：8

共 28 条

[1] New Benzimidazoles and Their Antitumor Effects with Aurora A Kinase and KSP Inhibitory Activities [J].

Abd El-All, Amira S. ;

Magd-El-Din, Asmaa A. ;

Ragab, Fatma A. F. ;

ElHefnawi, Mahmoud ;

Abdalla, Mohamed M. ;

Galal, Shadia A. ;

El-Rashedy, Ahmed A. .

ARCHIV DER PHARMAZIE, 2015, 348 (07) :475-486

[2] HYDROGEN-BONDING .32. AN ANALYSIS OF WATER-OCTANOL AND WATER-ALKANE PARTITIONING AND THE DELTA-LOG-P PARAMETER OF SEILER [J].

ABRAHAM, MH ;

CHADHA, HS ;

WHITING, GS ;

MITCHELL, RC .

JOURNAL OF PHARMACEUTICAL SCIENCES, 1994, 83 (08) :1085-1100

[3]

Ager DJ, 1998, ANGEW CHEM INT EDIT, V37, P1803

[4]

Brown B.S., 2006, Int. Patent Appl. Pub., Patent No. 2006065646

[5] Synthesis and structure-activity studies of novel orally active non-terpenoic 2,3-oxidosqualene cyclase inhibitors [J].

Dehmlow, H ;

Aebi, JD ;

Jolidon, S ;

Ji, YH ;

von der Mark, EM ;

Himber, J ;

Morand, OH .

JOURNAL OF MEDICINAL CHEMISTRY, 2003, 46 (15) :3354-3370

[6] Aryl piperazine melanocortin MC4 receptor agonists [J].

Dyck, B ;

Parker, J ;

Phillips, T ;

Carter, L ;

Murphy, B ;

Summers, R ;

Hermann, J ;

Baker, T ;

Cismowski, M ;

Saunders, J ;

Goodfellow, V .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2003, 13 (21) :3793-3796

[7] Synthesis, antimicrobial, and anti-HIV-1 activity of certain 5-(I-adamantyl)-2-substituted thio-1,3,4-oxadiazoles and 5-(1-adamantyl)-3-substituted aminomethyl-1,3,4-oxadiazoline-2-thiones [J].

El-Emam, AA ;

Al-Deeb, OA ;

Al-Omar, M ;

Lehmann, J .

BIOORGANIC & MEDICINAL CHEMISTRY, 2004, 12 (19) :5107-5113

[8] Use of N-methylpiperazine for the preparation of piperazine-based unsymmetrical bis-ureas as anti-HIV agents [J].

El-Faham, Ayman ;

Armand-Ugon, Mercedes ;

Este, Jose A. ;

Albericio, Fernando .

CHEMMEDCHEM, 2008, 3 (07) :1034-1037

[9] The chemistry of isothiazoles [J].

Elgazwy, ASSH .

TETRAHEDRON, 2003, 59 (38) :7445-7463

[10] Four-component, one-pot synthesis of spiropyrazolo pyrimidine derivatives by using recyclable nanocopper ferrite catalyst and antibacterial studies [J].

Ganta, Ravi Kumar ;

Ramgopal, A. ;

Ramesh, Chatragadda ;

Babu, K. Raghu ;

Kumar, M. Murali Krishna ;

Rao, B. Venkateswara .

SYNTHETIC COMMUNICATIONS, 2016, 46 (24) :1999-2008

← 1 2 3 →