cas 2382-96-9, 2-Mercaptobenzoxazole | Articles data

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Photoaddition Reactions of Benzoxazole-2(3H)-thiones to Cycloalkenes and Heteroaromatics
Photoaddition reactions of benzoxazole-2-thiones 1 with cycloalkenes 2 and heteroaromatics 3 were examined. Irradiation of N-acylbenzoxazole-2-thiones 1a and 1b, and 3-(methoxycarbonyl)- and 3-(phenoxycarbonyl)benzoxazole-2(3H)-thiones (1f and 1h, resp.)
Nishio, Takehiko,Shiwa, Kiyoko,Sakamoto, Masami
p. 3255 - 3264
(2003)
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Preparation method of mercapto-substituted nitrogen heterocyclic compound
The invention discloses a preparation method of sulfhydryl substituted nitrogen heterocyclic compounds. The preparation method comprises the following steps: a substituted aniline compound and a disulfide compound are subjected to a stirring reaction in an organic solvent at 60-150 DEG C for 1-15 h, after the reaction, a product is cooled to room temperature and dissolved and diluted by ethanol and water, then acid is added for acidification until pH reaches 1-6, and filtering and drying are performed finally. The preparation process is simple, low in cost and easy to operate and produces little environmental pollution.
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Paragraph 0044-0046

(2021/06/02)

Green synthesis of therapeutically active 1,3,4-oxadiazoles as antioxidants, selective COX-2 inhibitors and their in silico studies
A modest, competent and green synthetic procedure for novel coumarinyl-1,3,4-oxadiazolyl-2-mercaptobenzoxazoles 8i-t has been reported. Analysis of the docked (PDB ID: 5IKR; A-Chain) poses of the compounds illustrated that they adopt identical conformations to the extremely selective COX-2 inhibitor. The biological outcomes as well as computational study suggested that the compounds originated to have elevated resemblance towards COX-2 enzyme than COX-1. The compounds 8i, 8l, 8q, 8r, 8s and 8t emerged as most potent and selective COX-2 inhibitors in contrast with Mefenamic acid. The selectivity index of 8l, 8n and 8r was respectively found to be 33.95, 20.25 and 24.98 which manifested their high selectivity against COX-2. Interestingly, the compounds which were active as COX-2 inhibitors were also active as antioxidant agents.
Nesaragi, Aravind R.,Kamble, Ravindra R.,Dixit, Shruti,Kodasi, Barnabas,Hoolageri, Swati R.,Bayannavar, Praveen K.,Dasappa, Jagadeesh Prasad,Vootla, Shyamkumar,Joshi, Shrinivas D.,Kumbar, Vijay M.
supporting information

(2021/06/09)

A green approach for the synthesis of benzazolyl pyrimidinyl carbamothioates under ultrasonication and their antimicrobial activity
A library of benzazolyl pyrimidinyl carbamothioates were prepared by the reaction of benzazolyl carbonothioates with pyrimidinyl-2-amine in the presence of an ionic liquid- 1-butyl-3-methylimidazolium hydroxide ([bmim]OH) under ultrasonication at a frequency of 35?kHz and tested for antimicrobial activity. Chloro- and nitro-substituted benzothiazolyl/benzimidazolyl pyrimidinyl carbamothioates displayed prominent antibacterial activity against Bacillus subtilis, while nitro-substituted benzothiazolyl/benzimidazolyl pyrimidinyl carbamothioates showed excellent antifungal activity against Aspergilus niger. Graphic abstract: [Figure not available: see fulltext.].
Kayathi, Narendra Babu,Panga, Siva Sankar,Adivireddy, Padmaja,Venkatapuram, Padmavathi
p. 2931 - 2943
(2021/07/26)

Microwave facilitated one-pot three component synthesis of coumarin-benzoxazole clubbed 1,2,3-triazoles: Antimicrobial evaluation, molecular docking and in silico ADME studies
4-((4-((Benzo[d]oxazol-2-ylthio)methyl)-1H-1,2,3-triazol-1-yl)methyl)-2H-chromen-2-ones 7k–z were synthesized by conventional as well as microwave irradiation method in order to obtain antimicrobial agents. The present green synthetic protocol explores facile work up procedure with excellent yields (82–92%) and purity. Docking studies exhibited strong binding interactions with enzyme N-myristoyl transferase (PDB ID: 4CAW) with excellent C-score values. Compounds 7k–z were screened for their in vitro antimicrobial activities. The compounds 7w and 7 y exhibited excellent antimicrobial results for all the tested microorganisms at MICs ranging from 3.12 to 6.25 μg/ml in comparison with the marketed drugs.
Nesaragi, Aravind R.,Kamble, Ravindra R.,Bayannavar, Praveen K.,Metre, Tukaram V.,Kariduraganavar, Mahadevappa Y.,Margankop, Sheetal B.,Joshi, Shrinivas D.,Kumbar, Vijay M.
p. 3460 - 3472
(2021/10/02)

Synthesis, in?vitro biological screening and docking study of benzo[d]oxazole bis Schiff base derivatives as a potent anti-Alzheimer agent
We have synthesized benzo[d]oxazole derivatives (1–21) through a multistep reaction. Alteration in the structure of derivatives was brought in the last step via using various substituted aromatic aldehydes. In search of an anti-Alzheimer agent, all derivatives were evaluated against acetylcholinesterase and butyrylcholinesterase enzyme under positive control of standard drug donepezil (IC50 = 0.016 ± 0.12 and 4.5 ± 0.11 μM) respectively. In case of acetylcholinesterase enzyme inhibition, derivatives 8, 9 and 18 (IC50 = 0.50 ± 0.01, 0.90 ± 0.05 and 0.3 ± 0.05 μM) showed very promising inhibitory potentials. While in case of butyrylcholinesterase enzyme inhibition, most of the derivatives like 6, 8, 9, 13, 15, 18 and 19 (IC50 = 2.70 ± 0.10, 2.60 ± 0.10, 2.20 ± 0.10, 4.25 ± 0.10, 3.30 ± 0.10, 0.96 ± 0.05 and 3.20 ± 0.10 μM) displayed better inhibitory potential than donepezil. Moreover, derivative 18 is the most potent one among the series in both inhibitions. The binding interaction of derivatives with the active gorge of the enzyme was confirmed via a docking study. Furthermore, the binding interaction between derivatives and the active site of enzymes was correlated through the SAR study. Structures of all derivatives were confirmed through spectroscopic techniques such as 1H-NMR, 13C-NMR and HREI-MS, respectively. Communicated by Ramaswamy H. Sarma.
Alhibshi, Amani H.,Anouar, El Hassane,Khan, Khalid Mohammed,Nawaz, Faisal,Rahim, Fazal,Rehman, Ashfaq Ur,Sajid, Muhammad,Shah, Adnan Ali,Taha, Muhammad,Uddin, Nizam,Wadood, Abdul,Zaman, Khalid
(2022/01/14)

2-Mercaptobenzoxazoles: a class of carbonic anhydrase inhibitors with a novel binding mode to the enzyme active site
2-Mercaptobenzoxazole is a widely used organic scaffold in medicinal chemistry. By means of kinetic and structural studies, we demonstrate that this molecule can effectively be used to inhibit hCAs showing a peculiar binding mode. The results reported here can pave the way for the development of selective CA inhibitors. This journal is
Alterio, Vincenzo,Angeli, Andrea,Bozdag, Murat,Carta, Fabrizio,De Simone, Giuseppina,Esposito, Davide,Monti, Simona Maria,Supuran, Claudiu T.
supporting information
p. 8297 - 8300
(2020/08/17)

Three-Component Synthesis of 2-Alkylthiobenzoazoles in Aqueous Media
A highly efficient three-component protocol for the synthesis of the 2-alkylthiobenzoazoles is described. Tetramethylthiuram disulfide (TMTD) cyclized with o -aminothiophenols, generating the intermediate 2-mercaptobenzothiazoles, and the successive C-S coupling with halogenated alkanes afforded a series of 2-alkyl-substituted thiobenzothiazoles smoothly in a one-pot process. This procedure could also be utilized for the preparation of 2-alkyl-substituted thiobenzoxazoles and 2-alkyl-substituted thiobenzimidazoles. Inexpensive and easily available starting materials, metal catalyst-free, broad substrate scope, and water as solvent are the features of this protocol.
Chen, Jin-Quan,Dong, Zhi-Bing,Guo, Jia
p. 1927 - 1933
(2020/07/03)

HMOX1 inducers
The present invention is related to compounds of structure (I) as heme oxygenase 1 (HMOX 1) inducers. The present invention is also related a method of controlling the activity or the amount, or both the activity and the amount, of heme-oxygenase 1 in a mammalian subject. The definitions of the variables are provided herein.
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(2020/09/18)

Synthesis of thiocarbamoyl fluorides and isothiocyanates using amines with CF3SO2Cl
A practical and efficient method to synthesize thiocarbamyl fluorides and isothiocyanates from amines with trifluoromethanesulfonyl chloride was developed. In the presence of the reducing agent triphenylphosphine and sodium iodide, thiocarbamyl fluorides and isothiocyanates were synthesized from secondary/primary amine in moderate to excellent yields, respectively. A broad scope of substrates and good functional group compatibility were observed.
Jiang, Lvqi,Yi, Wenbin,Wei, Jingjing,Liang, Shuaishuai
p. 12374 - 12381
(2020/11/10)

Metal-free C–H mercaptalization of benzothiazoles and benzoxazoles using 1,3-propanedithiol as thiol source
A facile and effective C–H functionalization strategy for the synthesis of 2-mercaptobenzothiazoles and 2-mercaptobenzoxazoles is described. 1,3-Propanedithiol was employed to convert benzothiazoles and benzoxazoles to the corresponding heteroarylthiols in the presence of potassium hydroxide and DMSO. This novel protocol is featured by direct C–H mercaptalization of heteroarenes and a simple reaction system.
Xiao, Yan,Jing, Bing,Liu, Xiaoxia,Xue, Hongyu,Liu, Yajun
supporting information
p. 279 - 284
(2019/02/20)

Design, synthesis, molecular docking, and anticancer activity of benzoxazole derivatives as VEGFR-2 inhibitors
Novel series of benzoxazoles 4a-f-16 were designed, synthesized, and evaluated for anticancer activity against HepG2, HCT-116, and MCF-7 cells. HCT-116 was the most sensitive cell line to the influence of the new derivatives. In particular, compound 5e was found to be the most potent against HepG2, HCT-116, and MCF-7 with IC50 = 4.13 ± 0.2, 6.93 ± 0.3, and 8.67 ± 0.5 μM, respectively. Compounds 5c, 5f, 6b, 5d, and 6c showed the highest anticancer activities against HepG2 cells with IC50 of 5.93 ± 0.2, 6.58 ± 0.4, 8.10 ± 0.7, 8.75 ± 0.7, and 9.95 ± 0.9 μM, respectively; HCT-116 cells with IC50 of 7.14 ± 0.4, 9.10 ± 0.8, 7.91 ± 0.6, 9.52 ± 0.5, and 12.48 ± 1.1 μM, respectively; and MCF-7 cells with IC50 of 8.93 ± 0.6, 10.11 ± 0.9, 12.31 ± 1.0, 9.95 ± 0.8, and 15.70 ± 1.4 μM, respectively, compared with sorafenib as a reference drug with IC50 of 9.18 ± 0.6, 5.47 ± 0.3, and 7.26 ± 0.3 μM, respectively. The most active compounds 5c-f and 6b,c were further evaluated for their vascular endothelial growth factor receptor-2 (VEGFR-2) inhibition. Compounds 5e and 5c potently inhibited VEGFR-2 at lower IC50 values of 0.07 ± 0.01 and 0.08 ± 0.01 μM, respectively, compared with sorafenib (IC50 = 0.1 ± 0.02 μM). Compound 5f potently inhibited VEGFR-2 at low IC50 value (0.10 ± 0.02 μM) equipotent to sorafenib. Our design was based on the essential pharmacophoric features of the VEGFR-2 inhibitor sorafenib. Molecular docking was performed for all compounds to assess their binding pattern and affinity toward the VEGFR-2 active site.
El-Helby, Abdel-Ghany A.,Sakr, Helmy,Eissa, Ibrahim H.,Abulkhair, Hamada,Al-Karmalawy, Ahmed A.,El-Adl, Khaled
(2019/08/27)

Benzoxazole/benzothiazole-derived VEGFR-2 inhibitors: Design, synthesis, molecular docking, and anticancer evaluations
A novel series of benzoxazole/benzothiazole derivatives 4a–c–11a–e were designed, synthesized, and evaluated for anticancer activity against HepG2, HCT-116, and MCF-7 cells. HCT-116 was the most sensitive cell line to the influence of the new derivatives. In particular, compound 4c was found to be the most potent derivative against HepG2, HCT-116, and MCF-7 cells, with IC50 values = 9.45 ± 0.8, 5.76 ± 0.4, and 7.36 ± 0.5 μM, respectively. Compounds 4b, 9f, and 9c showed the highest anticancer activities against HepG2 cells with IC50 values of 9.97 ± 0.8, 9.99 ± 0.8, and 11.02 ± 1.0 μM, respectively, HCT-116 cells with IC50 values of 6.99 ± 0.5, 7.44 ± 0.4, and 8.15 ± 0.8 μM, respectively, and MCF-7 cells with IC50 values of 7.89 ± 0.7, 8.24 ± 0.7, and 9.32 ± 0.7 μM, respectively, in comparison with sorafenib as reference drug with IC50 values of 9.18 ± 0.6, 5.47 ± 0.3, and 7.26 ± 0.3 μM, respectively. The most active compounds 4a–c, 9b,c,e,f,h, and 11c,e were further evaluated for their VEGFR-2 inhibition. Compounds 4c and 4b potently inhibited VEGFR-2 at IC50 values of 0.12 ± 0.01 and 0.13 ± 0.02 μM, respectively, which are nearly equipotent to the sorafenib IC50 value (0.10 ± 0.02 μM). Furthermore, molecular docking studies were performed for all synthesized compounds to assess their binding pattern and affinity toward the VEGFR-2 active site.
El-Helby, Abdel-Ghany A.,Sakr, Helmy,Eissa, Ibrahim H.,Al-Karmalawy, Ahmed A.,El-Adl, Khaled
(2019/11/03)

Synthesis and biological evaluation of new 1,2,3-triazole based 2-sulfonylbenzoxazoles as potent anti-inflammatory and antibacterial agents
A novel series of 2-sulfonyl benzoxazoles containing 1,2,3-triazole nucleus was synthesized using highly efficient and environmentally benign microwave-assisted ionic liquids containing click synthesis. The newly synthesized compounds were screened for their anti-inflammatory and antibacterial activities. Among all the derivatives tested, compound 5c containing the 4-fluorophenyl group in the triazole ring exhibited the most potent anti-inflammatory activity and the remaining compounds have shown moderate to good activity compared to the reference drug. The antibacterial activity revealed that compound 5c has shown more potent activity than the standard drugs.
Ramesh Babu,Ravinder,Narsimha, Sirassu
p. 389 - 395
(2020/01/03)

A Highly Efficient Synthesis of 2-Benzimidazolthiones and Their Congeners under Mild Conditions
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Li, Wei-wei,Zheng, Hui
p. 175 - 181
(2019/04/17)

One-step construction of unsymmetrical thioureas and oxazolidinethiones from amines and carbon disulfide: Via a cascade reaction sequence
A concise and versatile method for the construction of unsymmetrical thioureas and oxazolidinethiones from amines and carbon disulfide has been achieved in DMSO without addition of extra reagents. The present protocol is compatible with various secondary amines and primary amines, and suitable for intermolecular and intramolecular reactions. Diverse unsymmetrical thioureas and oxazolidinethiones were efficiently obtained in good to excellent yields via a cascade reaction sequence.
Ding, Chaochao,Wang, Shaoli,Sheng, Yaoguang,Dai, Qian,Zhao, Yunjie,Liang, Guang,Song, Zengqiang
p. 26768 - 26772
(2019/09/06)

Preparation method of 2-mercaptobenzoxazole(thiazole) compounds taking 1,3-dimercaptopropane as mercapto source
The invention belongs to the synthesis field of medicine chemical intermediate, and provides a preparation method of 2-mercaptobenzoxazole(thiazole) compounds taking 1,3-dimercaptopropane as a mercapto source. According to the preparation method, under inert gas protection, in dimethyl sulphoxide solvent, substituted benzoxazole(thiazole) and 1,3-dimercaptopropane are subjected to 120 to 140 DEG Cheating stirring in the presence of an alkali, after 12 to 24h of reaction, an obtained reaction solution is cooled to room temperature, and is subjected to acidifying post-treatment so as to obtaina product. The reaction conditions are simple; function group compatibility is excellent; yield is relatively high; the obtained 2-mercaptobenzoxazole(thiazole) compounds are important organic synthesis intermediates; application range in the field of chemical raw material, pesticide, and medicine is wide; and practical value and social and economic benefit are excellent.
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(2018/10/02)

AlCl3-Promoted Synthesis of 2-Mercapto Benzoheterocycles by Using Sodium Dimethyldithiocarbamate as Thiocarbonyl Surrogate
A simple, expeditious and high-efficiency synthetic method for the AlCl3-mediated one-pot preparation of 2-mercapto benzoheterocycles (2-mercapto benzothiazoles, benzoxazoles and benzimidazoles) is described. By the treatment of a series of S, O and N heteroatoms containing bifunctional molecules with sodium dimethyldithiocarbamate in AlCl3, the desired benzoheterocycles are obtained smoothly. The protocol can also be applied on the synthesis of a series of thiazolidine-2-thiones, imidazolidine-2-thiones. This novel synthetic approach has advantages such as ligand-free, high efficiency, short reaction time, readily available starting materials and simple experimental procedures.
Liu, Xing,Zhang, Shi-Bo,Dong, Zhi-Bing
p. 5406 - 5411
(2018/10/20)

Copper(I)-Catalyzed Tandem One-Pot Synthesis of 2-Arylthiobenzothiazoles and 2-Arylthiobenzoxazoles in Water
An efficient tandem process for the preparation of 2-arylthiobenzothiazoles has been developed. By condensation of 2-aminobenzenethiol with tetramethylthiuram disulfide (TMTD), 2-mercaptobenzothiazoles was in situ generated, which susequently underwent coupling with iodobenzenes to give the desired 2-arylthiobenzothiazoles fluently in a one-pot manner. This method can also be used for the synthesis of 2-arylthiobenzoxazoles. Inexpensive metal catalyst and ligand, mild reaction temperature, and water as solvent make this protocol practically valuable and useful in organic synthesis.
Liu, Xing,Zhang, Shi-Bo,Zhu, Hui,Dong, Zhi-Bing
p. 11703 - 11711
(2018/10/02)

ANTIBIOTIC COMPOUNDS
The present invention relates to antibiotic compounds of formula (I), to compositions containing these compounds and to methods of treating bacterial diseases and infections using the compounds. The compounds find application in the treatment of infection with, and diseases caused by, Gram-positive and/or Gram-negative bacteria, and in particular in the treatment of infection with, and diseases caused by, Neisseria gonorrhoeae.
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Page/Page column 67; 68; 81; 82

(2018/03/25)

Method for preparing 2-chlorobenzoxazole and 2,6-dichlorobenzoxazole from o-aminophenol by taking solid triphosgene as chlorinating agent
The invention provides a method for preparing 2-chlorobenzoxazole and 2,6-dichlorobenzoxazole from o-aminophenol by taking solid triphosgene as a chlorinating agent. The method comprises the followingsteps: step 1, respectively preparing 2-benzoxazolone and 2-mercapto benzoxazole by taking the o-aminophenol as a raw material; step 2, preparing the 2-chlorobenzoxazole by taking the 2-mercapto benzoxazole as a raw material and the solid triphosgene as the chlorinating agent; step 3, preparing 6-chlorobenzoxazolone by taking TCCA and the 2-benzoxazolone as raw materials; step 4, preparing 2-mercapto-6-chlorobenzoxazole; step 5, preparing the 2,6-dichlorobenzoxazole by taking the 2-mercapto-6-chlorobenzoxazole as a raw material and the solid triphosgene as the chlorinating agent. The method provided by the invention is a brand-new preparation method, which has the advantages of less corrosion to equipment, high yield, less reaction time, mild reaction conditions, less by-products and reduced environmental pollution.
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(2018/12/05)

Novel benzoxazole derivatives featuring rhodanine and analogs as antihypergycemic agents: synthesis, molecular docking, and biological studies
A novel series of benzoxazolyl linked benzylidene based rhodanine and their cyclic analogs were synthesized, characterized and evaluated for their α-amyloglucosidase inhibitory activity. Out of eight target compounds, two compounds (4b and 5b) displayed potent inhibitory activity against α-amyloglucosidase with IC50 values in the range of 0.24 ± 0.01–0.94 ± 0.01 μM as compared to standard drug acarbose. Among all the tested compounds, compound 5b containing rhodanine at 3-position of phenyl was found to be the most active inhibitor of α-amyloglucosidase. Docking studies showed the existence of potential H-bonding interactions between synthesized compounds and α-glucosidase which might be responsible for good biological activity.
Singh, Varinder,Singh, Amanjot,Singh, Gagandeep,Verma, Raman K.,Mall, Rajiv
p. 735 - 743
(2017/10/25)

Elemental sulfur as a sulfuration agent in the copper-catalyzed C-H bond thiolation of electron-deficient arenes
By utilizing elemental sulfur as the thiolation agent and oxidant, a copper-catalyzed direct C-H bond thiolation of electron-deficient arenes was demonstrated. Various electron-deficient arenes were proved to be suitable for this transformation. Preliminary mechanistic studies indicated that this reaction underwent a radical pathway, in which the trisulfur radical anion (S3-) might play a vital role. Meanwhile, KIE experiments suggested that C-H bond cleavage was not involved in the rate-determining step.
Yan, Haiming,Huang, Zhiliang,Chen, Meng,Li, Cuiting,Chen, Ya,Gao, Meng,Lei, Aiwen
supporting information
p. 8276 - 8279
(2017/10/23)

An environmentally benign and efficient synthesis of substituted benzothiazole-2-thiols, benzoxazole-2-thiols, and benzimidazoline-2-thiones in water
An efficient and practical method for the one-step synthesis of benzothiazole-2-thiols, benzoxazole-2-thiols and benzimidazoline-2-thiones by cyclization of 2-aminothiophenols, 2-aminophenols, and 1,2-phenylenediamines with tetramethylthiuram disulfide (TMTD) in water was described. The features of this method include metal/ligand-free, excellent yield, short reaction time and broad substrate scope. The method provides a facile and convenient preparation of some potentially biologically active compounds.
Liu, Xing,Liu, Min,Xu, Wan,Zeng, Meng-Tian,Zhu, Hui,Chang, Cai-Zhu,Dong, Zhi-Bing
p. 5591 - 5598
(2017/12/06)

Selective synthesis of 2-aminobenzoxazoles and 2-mercaptobenzoxazoles by using o-aminophenols as starting material
2-Aminobenzoxazoles and 2-mercaptobenzoxazoles were selectively synthesized by treating o-aminophenols with dithiocarbamates and tetramethylthiuram disulfide (TMTD), respectively. With the promotion of NaH/CuI, the reaction of o-aminophenols with dithioca
Liu, Min,Zeng, Meng-Tian,Xu, Wan,Wu, Li,Dong, Zhi-Bing
supporting information
p. 4352 - 4356
(2017/10/17)

OCTAHYDROPYRROLO [3, 4-c] PYRROLE DERIVATIVES AND USES THEREOF
The invention relates to octahydropyrrolo [3, 4-c] pyrrole derivatives and uses thereof. Compounds and pharmaceutical compositions comprising the compounds provided herein are used for antagonizing orexin receptors. The invention also relates to processes for preparing the compounds and pharmaceutical compositions, and uses thereof in treating or preventing a disease related to orexin receptors.
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Paragraph 00186; 00209

(2017/07/04)

Synthesis and Antibacterial Activity of Sulfur-linked Bis and Tris Heterocycles
The bis and tris heterocycles-benzoxazolyl/benzothiazolyl/benzimidazolyl quinazolines linked by sulfur and/or nitrogen were prepared from 2,4-dichloroquinazoline and benzazolyl-2-thiol/benzazolyl-2-amine and studied their antibacterial activity. The nitro-substituted sulfur-linked bisbenzothiazolylquinazoline (12f), bisbenzimidazolylquinazoline (13f), and nitro-substituted sulfur and nitrogen-linked bisbenzothiazolylquinazoline (15f) were found to be potential antibacterial agents against Staphylococcus aureus.
Mallikarjuna Reddy,Lavanya,Lakshmi Teja,Padmaja,Padmavathi
p. 2755 - 2766
(2017/09/26)

Isothiocyanation of amines using the Langlois reagent
The Langlois reagent was found to be effective for the isothiocyanation of primary amines in the presence of copper iodide and diethyl phosphonate.
Liao, Yan-Yan,Deng, Jian-Chao,Ke, Yan-Ping,Zhong, Xiao-Lin,Xu, Li,Tang, Ri-Yuan,Zheng, Wenxu
supporting information
p. 6073 - 6076
(2017/07/10)

Selective: S -arylation of 2-oxazolidinethiones and selective N -arylation of 2-benzoxazolinones/2-benzimidazolinones
There exist three possible patterns for the reaction of cyclic 2-oxazolidinethione and 2-benzoxazolidinethione with arynes, namely (a) S-arylation, (b) N-arylation, and (c) aryne insertion into the thiocarbonyl group (CS). Our studies demonstrate that S-arylation wins out affording S-aryl dihydrooxazoles. In contrast, for related reactions of cyclic 2-benzoxazolinone and 2-benzimidazolinone with arynes, it is found that N-arylation outcompetes O-arylation and aryne insertion into the CO group to give N-aryl 2-benzoxazolinones and N-aryl 2-benzimidazolinones.
Sun, Chu-Han,Lu, Yi,Zhang, Qing,Lu, Rong,Bao, Lin-Qing,Shen, Mei-Hua,Xu, Hua-Dong
supporting information
p. 4058 - 4063
(2017/07/10)

Synthesis, biological evaluation and molecular docking study of N-arylbenzo[d]oxazol-2-amines as potential α-glucosidase inhibitors
A novel series of N-arylbenzo[d]oxazol-2-amines (4a–4m) were synthesized and evaluated for their α-glucosidase inhibitory activity. Compounds 4f–4i, 4k and 4m displayed potent inhibitory activity against α-glucosidase with IC50values in the range of 32.49?±?0.17–120.24?±?0.51?μM as compared to the standard drug acarbose. Among all tested compounds, compound 4g having 4-phenoxy substitution at the phenyl ring was found to be the most active inhibitor of α-glucosidase with an IC50value of 32.49?±?0.17?μM. Analysis of the kinetics of enzyme inhibition indicated that compound 4g is a noncompetitive inhibitor of α-glucosidase with a Kivalue of 31.33?μM. Binding interaction of compound 4g with α-glucosidase was explored by molecular docking simulation.
Wang, Guangcheng,Peng, Zhiyun,Wang, Jing,Li, Juan,Li, Xin
p. 5374 - 5379
(2016/10/22)

Synthesis of Benzoxazolylthiomethyl and Benzthiazolylthiomethyl Quinazolin-4(3 h)-ones
o-Aminophenol (1a, X = O) or o-aminothiophenol (1b, X = S) was reacted with carbon disulfide in ethanol containing KOH under reflux to obtain 2-mercaptobenzoxazole (2a, X = O) and 2-mercaptobenzthiazole (2b, X = S), respectively. Condensation of 2a and 2b each with chloroacetic acid gave 2-(benzoxazol-2-ylthio)acetic acid (3a, X = O) and 2-(benzthiazol-2-ylthio)acetic acid (3b, X = S) respectively which with anthranilamide gave 2-((benzoxal-2-ylthio)methyl) quinazolin-4(3H)-one (5a, X = O) and 2-((benzthiazol-2-ylthio)methyl)quinazolin-4(3H)-one (5b, X = S) respectively. The products 5a,b could be prepared in three other routes involving the general sequences 6→2→5, 6→7→5 and 8→9→5.
Rafeeq, Mohammad,Ramana Reddy, Chittireddy Venkata,Dubey, Pramod Kumar
p. 1857 - 1864
(2015/12/12)

Design, synthesis and biological evaluation of bivalent benzoxazolone and benzothiazolone ligands as potential anti-inflammatory/analgesic agents
Abstract Benzoxazolone and benzothiazolone were used as template blocks to develop two series of dimers as anti-inflammatory and analgesic agents based on the concept of bivalent ligands. The first series (I) involved varying the carbon chain lengths extending from the piperazine core to the nitrogen atom of the dibenzo[d]oxazol-2(3H)-one or dibenzo[d]thiazol-2(3H)-one. The second series (II) was designed by changing the attachment point. All compounds were screened for their in vitro anti-inflammatory activity in terms of the inhibition of inducible nitric oxide synthase (iNOS) and nuclear factor kappa B (NF-κB). Seventeen compounds inhibited both targets. Eleven of them exhibited IC50 values below 3 μM while five compounds showed IC50 values of 1 μM or below. Most of the compounds were found to be devoid of cytotoxicity against mammalian kidney and solid tumors cell lines up to 25 μg/mL. In vivo anti-inflammatory and antinociceptive studies revealed that compounds 3j, 5t and 8b have significant anti-inflammatory and analgesic activity comparable to that of indomethacin and ketorolac, respectively.
Abdelazeem, Ahmed H.,Khan, Shabana I.,White, Stephen W.,Sufka, Kenneth J.,McCurdy, Christopher R.
p. 3248 - 3259
(2015/08/03)

2-Aminobenzoxazole ligands of the hepatitis C virus internal ribosome entry site
2-Aminobenzoxazoles have been synthesized as ligands for the hepatitis C virus (HCV) internal ribosome entry site (IRES) RNA. The compounds were designed to explore the less basic benzoxazole system as a replacement for the core scaffold in previously discovered benzimidazole viral translation inhibitors. Structure-activity relationships in the target binding of substituted benzoxazole ligands were investigated.
Rynearson, Kevin D.,Charrette, Brian,Gabriel, Christopher,Moreno, Jesus,Boerneke, Mark A.,Dibrov, Sergey M.,Hermann, Thomas
p. 3521 - 3525
(2014/07/22)

Regioselective thiolation of arenes and heteroarenes: C-H functionalization strategy for C-S bond formation
A facile transition-metal-free oxidative cross-dehydrogenative coupling reaction involving selective formation of a C-S bond leading to the synthesis of arylthiobenzoxazoles, heteroarylthiobenzoxazoles, and arylthiobenzothiazoles has been described. This highly regioselective C-H functionalization reaction with electron-rich aromatic systems including heteroaromatics is achieved by reversing the reactivity of sulfur in the presence of a suitable oxidant and strong acid. (Chemical Equation Presented).
Varun, Begur Vasanthkumar,Prabhu, Kandikere Ramaiah
p. 9655 - 9668
(2015/01/16)

Lanthanide-catalyzed cyclocarbonylation and cyclothiocarbonylation: A facile synthesis of benzannulated 1,3-diheteroatom five- and six-membered heterocycles
La[N(SiMe3)2]3 proves to be an efficient catalyst system for the cyclocarbonylation of 1,2-disubstituted benzenes with isocyanates. In this approach, aryl/alkyl isocyanates react with o-phenylenediamine, o-aminophenol, o-aminothiophenol, catechols and anilines ortho-substituted by CH2NH2 and CONH2 to form, respectively, the corresponding benzimidazolones, benzoxazolones, benzothiazolones, benzodioxolones, 3,4-dihydroquinazolin-2(1H)-one, and quinazolinediones. These results represent the first example of lanthanide-catalyzed carbonylation. This methodology is also applicable for the preparation of various benzannulated 1,3-diheteroatom cyclic thioketones starting from aryl/alkyl isothiocyanates or CS2 in good to excellent yields. Based on the results of experiments performed using an o-aminobenzamido dianion lanthanide complex, a general mechanism, involving the tandem reaction of two lanthanide-ligand bonds with one heterocumulene molecule, is proposed as well.
Jing, Yufeng,Liu, Ruiting,Lin, Yanghui,Zhou, Xigeng
p. 1117 - 1125
(2014/08/18)

Synthesis and insecticidal activity of novel dihalopropene derivatives containing benzoxazole moiety: A structure-activity relationship study
Ten dichloropropene derivatives containing benzoxazole moiety were synthesized and bioassayed in order to determine their in vivo insecticidal activity. The structures of obtained compounds were identified by 1H NMR, MS and elemental analyses. The bioassay results indicated that compound 2-(3-(2,6-dichloro-4-(3,3-dichloroallyloxy)phenoxy)propoxy)-5-(trifluoromethyl) benzo[d]oxazole (5i, R1 is trifluoromethyl, R2 is H and n is 3) had the optimal structure with best insecticidal activity against Spodoptera exigua (100%) at 1 mg/L concentration, highlighting the importance of trifluoromethyl group. The structure-activity relationship of the synthesized compounds was discussed as well.
Guan, Aiying,Qin, Yukun,Wang, Junfeng,Li, Bin
p. 120 - 123
(2013/11/06)

Synthesis of new chiral ferrocenyl P,N-ligands with a benzoxazole ring and their application in Ag-catalyzed asymmetric [3+2] cycloaddition
New chiral ferrocenyl P,N-ligands with a benzoxazole ring as the N-donor group have been synthesized from 2-aminophenol through a three-step transformation and successfully employed in the Ag-catalyzed asymmetric [3+2] cycloaddition of azomethine ylides with electron-deficient alkenes. High diastereoselectivities, excellent enantioselectivities, and good yields have been achieved for a variety of substrates, demonstrating the potential of these new P,N-ligands in asymmetric catalysis.
Yan, Sheng,Zhang, Cheng,Wang, Ya-Hui,Cao, Zhong,Zheng, Zhuo,Hu, Xiang-Ping
supporting information
p. 3669 - 3672
(2013/07/11)

Synthesis of thioureas in ionic liquid medium
A highly efficient procedure for the synthesis of symmetrical thioureas by means of simple condensation of primary amines and carbon disulfide in 1-butyl-3-methylimidazolium chloride [BMIM][Cl] as a cheap and commercially available ionic liquid is presented. This procedure works for aromatic and aliphatic primary amines and give high to excellent yields of symmetrical thioureas without need for any catalyst or tedious work-up.
Halimehjani, Azim Ziyaei,Farahbakhsh, Fataneh
p. 284 - 288
(2013/08/26)

Utilization of carbon disulfide as a powerful building block for the synthesis of 2-aminobenzoxazoles
This protocol describes a novel, mild and convenient route to afford 2-aminobenzoxazoles in high yields, and represents a significant advance towards an environmentally friendly strategy. Aliphatic amines are made to react with carbon disulfide to provide intermediate dithiocarbamates (DTC), which in the presence of 2-aminophenol, subsequently undergo successive intermolecular nucleophilic attack and desulfurization to produce 2-aminobenzoxazoles within 3 h.
Guntreddi, Tirumaleswararao,Allam, Bharat Kumar,Singh, Krishna Nand
p. 9875 - 9880
(2013/09/02)

An expeditious microwave-assisted synthesis of mercapto benzazoles, quinazolinone and oxadiazoles
A simple, convenient and high yielding synthetic method for the preparation of various mercapto derivatives of benzimidazoles 2a-e, benzoxazole 2f, benzothiazole 2g, quinazolinone 2h, 5- substituted-1,3,4-oxadiazoles 4a-f by the treatment of a series of O, S and N heteroatoms containing bifunctional molecules with potassium isopropyldithiocarbonate under microwave irradiation technique is described.
Mahesh Kumar,Dubey
p. 1619 - 1622
(2013/01/15)

Preparation, antibacterial evaluation and preliminary structure-activity relationship (SAR) study of benzothiazol- and benzoxazol-2-amine derivatives
In this study, a novel benzothiazol- and benzooxazol-2-amine scaffold with antibacterial activity was designed and synthesized. Preliminary structure-activity relationship analysis displayed that compound 8t with a 5,6-difluorosubstituted benzothiazole was found to be a potent inhibitor of Gram-positive pathogens, and exhibited some potential against drug-resistant bacteria and without cytotoxicity in therapeutic concentrations. In addition, molecular docking studies indicated that Staphylococcus aureus methionyl-tRNA synthetase might be the possible target of these compounds. Taken together, the present study provides an effective entry to the synthesis of a good lead for subsequent optimization and a new small molecule candidate drug for antibacterial therapeutics.
Ouyang, Liang,Huang, Yuhui,Zhao, Yuwei,He, Gu,Xie, Yongmei,Liu, Jie,He, Jun,Liu, Bo,Wei, Yuquan
supporting information; experimental part
p. 3044 - 3049
(2012/06/04)

An environmentally benign procedure for the synthesis of substituted 2-thiobenzothiazoles, 2-thiobenzoxazoles, 2-thiobenzimidazoles, and 1,3-oxazolopyridine-2-thiols
An improved environmentally benign procedure for the synthesis of substituted 2-thio-benzothia(oxa)zoles, 2-thiobenzimidazoles, and 1,3-oxazolopyridine-2-thiols by cyclization of 2-aminophenols, 2-aminothiophenols, 1,2-phenylenediamines, or 2-amino-3-hydroxypyridines with potassium O-ethyldithiocarbonate in PEG 400 or glycerol under directed microwave irradiation is described. The method can be applied to the synthesis of a variety of derivatives. Springer-Verlag 2011.
Deligeorgiev, Todor G.,Kaloyanova, Stefka S.,Lesev, Nedyalko Y.,Vaquero, Juan J.
experimental part
p. 895 - 899
(2012/01/06)

CsF-Celite catalyzed facile N-alkylation of 2(3H)-benzoxazolones and antimicrobial properties of 2-substituted benzoxazole and 3-substituted-2(3H)- benzoxazolone derivatives
The synthesis and antimicrobial activity studies of a new series of cyclic amine containing benzoxazoles and benzoxazolone-2(3H)-ones derivatives were described. The alkylation of benzoxazolone was carried out using cesium fluoride-Celite. The newly synthesized compounds with the influence of the induction of the cyclic amine moiety in the benzoxazole scaffold have been evaluated with respect to the antibacterial and antifungal activity. The 2-cyclic amine-1,3-benzoxazoles (5a-l), 5-chloro-3-alkyl substituted-1,3- benzoxazol-2(3H)-ones (8a-f), and 3-[3- (cyclic amine)propyl]-1,3-benzoxazol- 2(3H)-ones (9a-f) were synthesized. These derivatives were tested for antibacterial and antifungal activity. Among the compounds tested, 8c and 9f showed moderate to good antibacterial and antifungal activity. Compound 8a showed good antifungal activity. Springer Science+Business Media, LLC 2010.
Murty,Ram, Kesur R.,Rao, Rayudu Venkateswara,Yadav,Murty,Kumar, K. Pranay
scheme or table
p. 626 - 636
(2012/04/04)

Synthesis and preliminary evaluation of 2-substituted-1,3-benzoxazole and 3-[(3-substituted)propyl]-1,3-benzoxazol-2(3H)-one derivatives as potent anticancer agents
The synthesis and cytotoxic activity studies of a new series of cyclic amine containing benzoxazole and benzoxazolone derivatives are described. The 2-cyclic amine-1,3-benzoxazoles 5a-k, 5-chloro-3-(3-chloropropyl)- 1,3-benzoxazol-2(3H)-one 8 and 3-[3-(cyclic amino)- propyl]-1,3-benzoxazol-2(3H) -ones 9a-f were synthesized. The newly synthesized compounds with the influence of the presence of cyclic amine moiety in the benzoxazole scaffold have been evaluated with respect to their cytotoxic effect toward four human cancer cell lines. The new compounds were evaluated to see whether substitution at the second and third position of the benzoxazole motif influence their cytotoxic effect toward cancer cells. Springer Science+Business Media, LLC 2011.
Murty,Ram, Kesur R.,Rao, Rayudu Venkateswara,Yadav,Rao, Janapala Venkateswara,Cheriyan, Vino T.,Anto, Ruby John
scheme or table
p. 576 - 586
(2012/04/04)

The first low μM SecA inhibitors
SecA ATPase is a critical member of the Sec family, which is important in the translocation of membrane and secreted polypeptides/proteins in bacteria. Small molecule inhibitors can be very useful research tools as well as leads for future antimicrobial agent development. Based on previous virtual screening work, we optimized the structures of two hit compounds and obtained SecA ATPase inhibitors with IC50 in the single digit micromolar range. These represent the first low micromolar synthetic inhibitors of bacterial SecA and will be very useful for mechanistic studies.
Chen, Weixuan,Huang, Ying-ju,Gundala, Sushma Reddy,Yang, Hsiuchin,Li, Minyong,Tai, Phang C.,Wang, Binghe
experimental part
p. 1617 - 1625
(2010/05/17)

Synthesis and characterization of oxazolopyridine and benzoxazole derivatives
Synthesis of piperazinyl-substituted oxazolopyridine and benzoxazole was achieved in three steps starting from aminophenol and carbon disulfide. Condensation of aminophenols with carbon disulfide in ethanol using potassium hydroxide as catalyst gave the required benzoxazole thiol in one step. Treatment of the thiol with piperazine and substituted piperazine derivatives in toluene furnished the titled compounds in good yield. We introduced halogen substitution in the pendant arm of the piperazine derivatives for versatile functionalization. We report the synthesis and characterization of these compounds using high resolution NMR techniques.
Venkatachalam,Pierens,Reutens
p. 519 - 527
(2015/03/03)

Synthesis, crystal and antibacterial studies of diversely functionalized tetrahydropyridin-4-ol
In an effort to expand the spectrum of antibacterial activity associated with piperidin-4-one derivatives, we have synthesized two series of 3-carboxyethyl-2,6-diphenyl-4-hydroxy-Δ3-tetrahydropyridine derivatives bearing diversified heterocyclic and aromatic systems at the nitrogen atom through acetyl (6-18) and 2-propanoyl (9-31) linkers. Unlike acetyl derivatives, NMR spectral pattern of the propanoyl counterparts revealed the existence of pair of rotational isomers (syn and anti) in solution at room temperature due to the hindered rotation about N-CO bond. X-ray crystal studies of 9 and 24 clearly pointed out that all the compounds existed in only one form particularly, in stable syn form in solid state. Each of the compounds was screened for their in vitro antibacterial activity against nine human pathogenic Gram-positive strains including multiple drug resistant organisms and seven problematic Gram-negative strains. Among the various heterocycles examined here, imidazole substituted derivatives 12 and 25 exhibited antibacterial activity approaching that of Linezolid and Trovafloxacin drugs particularly against multiple resistant Enterococcus faecium-VanA phenotype strains.
Aridoss, Gopalakrishnan,Amirthaganesan, Shanmugasundaram,Jeong, Yeon Tae
supporting information; experimental part
p. 2242 - 2249
(2010/07/05)

Antimicrobial and analgesic evaluation of newly synthesized benzoxazole incorporated azitidinones
The cyclocondensation of the Schiff s bases 5(a-j) with chloroacetyl chloride in presence of triethyl amine resulted in the formation of 2-(1,3-benzoxazole-2-yl thio)-N-(3-chloro-2-oxo-4-phenylazetidin-1-yl) acetamide analogs 6(a-j). The structures of the newly synthesized compounds have been established by IR, 1H NMR and mass spectral studies. All the synthesized compounds have been screened for antimicrobial and analgesic activities.
Hanumanthappa,Vagdevi,Vaidya,Srikrishna,Raghavendra
p. 121 - 124
(2013/09/23)

In situ generation and trapping of aryllithium and arylpotassium species by halogen, sulfur, and carbon electrophiles
(Chemical Equation Presented) A general method has been developed for in situ trapping of arylmetal intermediates by halogen, sulfur, ketone, and aldehyde electrophiles affording the functionalization of the most acidic position in arene. Pentafluorobenzene, benzothiazole, and benzoxazole can be functionalized by using K3PO4 base. For less acidic arenes, tBuOLi base is required. Arenes with DMSO pKa values of 35 or less are reactive. 2009 American Chemical Society.
Popov, Ilya,Do, Hien-Quang,Daugulis, Olafs
supporting information; experimental part
p. 8309 - 8313
(2010/01/16)

Synthesis and use of achiral oxazolidine-2-thiones in selective preparation of trans 2,5-disubstituted tetrahydrofurans
The use of achiral N-acetyloxazolidine-2-thiones in the C-glycosylation of lactol acetates has allowed us to prepare with high diastereoselectivity the expected trans 2,5-disubstituted tetrahydrofurans. A study based on the role of the steric hindrance of the N-acetyloxazolidine-2-thiones is reported. Wiley-VCH Verlag GmbH & Co. KGaA, 2009.
Jalce, Gael,Franck, Xavier,Figadere, Bruno
experimental part
p. 378 - 386
(2009/09/25)

Conversion of a highly selective sigma-1 receptor-ligand to sigma-2 receptor preferring ligands with anticocaine activity
Cocaine's toxicity can be mitigated by blocking its interaction with sigma-1 receptors. The involvement of sigma-2 receptors remains unclear. To investigate their potential role, we have designed compounds through a convergent synthesis utilizing a highly selective sigma-1 ligand and elements of a selective sigma-2 ligand. Among the synthesized compounds was produced a subnanomolar sigma-2 ligand with an 11-fold preference over sigma-1 receptors. These compounds may be useful in developing effective pharmacotherapies for cocaine toxicity.
Mésangeau, Christophe,Narayanan, Sanju,Green, Andrea M.,Shaikh, Jamaluddin,Kaushal, Nidhi,Viard, Eddy,Xu, Yan-Tong,Fishback, James A.,Poupaert, Jacques H.,Matsumoto, Rae R.,McCurdy, Christopher R.
p. 1482 - 1486
(2008/09/20)