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Article: Synthesis and characterization of amide linked triazolyl glycolipids as molecular hydrogelators and organogelators

Wang, Guijun / Chen, Anji / Mangunuru, Hari P. R / Yerabolu, Jayasudhan Reddy

RSC advances. 2017 Aug. 22, v. 7, no. 65

2017

Abstract: Carbohydrate based small molecular gelators are important classes of compounds which can form useful soft materials with many practical applications. Although many different types of effective gelators have been reported, the rational design of a ... ...

Abstract	Carbohydrate based small molecular gelators are important classes of compounds which can form useful soft materials with many practical applications. Although many different types of effective gelators have been reported, the rational design of a molecular hydrogelator is still challenging. In this research, we combined the structural features of two classes of monosaccharide based molecular gelators and obtained a new class of glycolipids that can function as molecular gelators. These new compounds were synthesized by introducing a triazole functional group to a protected 2-glucosamine through Cu(i) catalyzed azide/alkyne cycloaddition reaction (CuAAC). A series of eighteen new glycolipids containing 4,6-O-benzylidene acetal protected d-glucosamide and triazole were synthesized and characterized. The self-assembling properties of these compounds were screened in several organic solvents, aqueous solutions, and water. All eighteen compounds are effective molecular gelators for at least one solvent and, more significantly, eleven compounds are hydrogelators with minimum gelation concentrations of 0.15–1.0 wt%. The hydrogels are suitable carriers for sustained release of chloramphenicol, and for the entrapment of toluidine blue dye. These results indicate that the d-glucosamide triazoles are effective templates for small molecular hydrogelators and are useful in designing sugar based soft materials.
Keywords	alkynes ; aqueous solutions ; azides ; chloramphenicol ; copper ; cycloaddition reactions ; gelation ; glycolipids ; hydrogels ; moieties ; solvents ; sugars ; toluidine blue ; triazoles
Language	English
Dates of publication	2017-0822
Size	p. 40887-40895.
Publishing place	The Royal Society of Chemistry
Document type	Article
ISSN	2046-2069
DOI	10.1039/c7ra06228a
Database	NAL-Catalogue (AGRICOLA)

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Article: Synthesis of peptoid based small molecular gelators by a multiple component reaction

Mangunuru, Hari P. R / Wang, Guijun / Yang, Hao

Chemical communications. 2013 Apr. 23, v. 49, no. 40

2013

Abstract: We report the synthesis and self-assembling properties of a new class of tripeptoids synthesized by a one-pot Ugi reaction from simple starting materials. Among the focused library of tripeptoids synthesized, several efficient low molecular weight ... ...

Abstract	We report the synthesis and self-assembling properties of a new class of tripeptoids synthesized by a one-pot Ugi reaction from simple starting materials. Among the focused library of tripeptoids synthesized, several efficient low molecular weight gelators were obtained for aqueous DMSO and ethanol mixtures.
Keywords	chemical communication ; chemical reactions ; dimethyl sulfoxide ; ethanol ; molecular weight ; N-substituted glycines
Language	English
Dates of publication	2013-0423
Size	p. 4489-4491.
Publishing place	The Royal Society of Chemistry
Document type	Article
ZDB-ID	1472881-3
ISSN	1364-548X ; 1359-7345 ; 0009-241X
ISSN (online)	1364-548X
ISSN	1359-7345 ; 0009-241X
DOI	10.1039/c3cc41043a
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Article ; Online: Synthesis of Chiral 1,2-Amino Alcohol-Containing Compounds Utilizing Ruthenium-Catalyzed Asymmetric Transfer Hydrogenation of Unprotected α-Ketoamines.

Mangunuru, Hari P R / Terrab, Leila / Janganati, Venumadhav / Kalikinidi, Nageswara Rao / Tenneti, Srinivasarao / Natarajan, Vasudevan / Shada, Arun D R / Naini, Santhosh Reddy / Gajula, Praveen / Lee, Daniel / Samankumara, Lalith P / Mamunooru, Manasa / Jayaraman, Aravindan / Sahani, Rajkumar Lalji / Yin, Jinya / Hewa-Rahinduwage, Chathuranga C / Gangu, Aravind / Chen, Anji / Wang, Zhirui /

Desai, Bimbisar / Yue, Tai Y / Wannere, Chaitanya S / Armstrong, Joseph D / Donsbach, Kai O / Sirasani, Gopal / Gupton, B Frank / Qu, Bo / Senanayake, Chris H

The Journal of organic chemistry

2024 Volume 89, Issue 9, Page(s) 6085–6099

Abstract: Herein, we disclose a facile synthetic strategy to access an important class of drug molecules that contain chiral 1,2-amino alcohol functionality utilizing highly effective ruthenium-catalyzed asymmetric transfer hydrogenation of unprotected α- ... ...

Abstract	Herein, we disclose a facile synthetic strategy to access an important class of drug molecules that contain chiral 1,2-amino alcohol functionality utilizing highly effective ruthenium-catalyzed asymmetric transfer hydrogenation of unprotected α-ketoamines. Recently, the COVID-19 pandemic has caused a crisis of shortage of many important drugs, especially norepinephrine and epinephrine, for the treatment of anaphylaxis and hypotension because of the increased demand. Unfortunately, the existing technologies are not fulfilling the worldwide requirement due to the existing lengthy synthetic protocols that require additional protection and deprotection steps. We identified a facile synthetic protocol via a highly enantioselective one-step process for epinephrine and a two-step process for norepinephrine starting from unprotected α-ketoamines
MeSH term(s)	Hydrogenation ; Catalysis ; Amino Alcohols/chemistry ; Amino Alcohols/chemical synthesis ; Ruthenium/chemistry ; Stereoisomerism ; Molecular Structure ; Amines/chemistry
Chemical Substances	Amino Alcohols ; Ruthenium (7UI0TKC3U5) ; Amines
Language	English
Publishing date	2024-04-22
Publishing country	United States
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	123490-0
ISSN	1520-6904 ; 0022-3263
ISSN (online)	1520-6904
ISSN	0022-3263
DOI	10.1021/acs.joc.4c00045
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Article ; Online: Synthesis of peptoid based small molecular gelators by a multiple component reaction.

Mangunuru, Hari P R / Yang, Hao / Wang, Guijun

Chemical communications (Cambridge, England)

2013 Volume 49, Issue 40, Page(s) 4489–4491

Abstract	We report the synthesis and self-assembling properties of a new class of tripeptoids synthesized by a one-pot Ugi reaction from simple starting materials. Among the focused library of tripeptoids synthesized, several efficient low molecular weight gelators were obtained for aqueous DMSO and ethanol mixtures.
MeSH term(s)	Gels/chemical synthesis ; Gels/chemistry ; Molecular Structure ; Molecular Weight ; Particle Size ; Peptoids/chemical synthesis ; Peptoids/chemistry ; Surface Properties
Chemical Substances	Gels ; Peptoids
Language	English
Publishing date	2013-05-18
Publishing country	England
Document type	Journal Article ; Research Support, U.S. Gov't, Non-P.H.S.
ZDB-ID	1472881-3
ISSN	1364-548X ; 1359-7345 ; 0009-241X
ISSN (online)	1364-548X
ISSN	1359-7345 ; 0009-241X
DOI	10.1039/c3cc41043a
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Article: Synthesis of a series of glucosyl triazole derivatives and their self-assembling properties

Mangunuru, Hari P.R / Dong Liu / Guijun Wang / Jayasudhan R. Yerabolu

Tetrahedron letters. 2015 Jan. 01, v. 56, no. 1

2015

Abstract: We report the synthesis and self-assembling properties of a new class of glucosyl triazole derivatives from glucose. The compounds are synthesized by a Cu(I) catalyzed azide/alkyne cycloaddition reaction, or the ‘click’ reaction. Several efficient low ... ...

Abstract	We report the synthesis and self-assembling properties of a new class of glucosyl triazole derivatives from glucose. The compounds are synthesized by a Cu(I) catalyzed azide/alkyne cycloaddition reaction, or the ‘click’ reaction. Several efficient low molecular weight organogelators were obtained in this study. We found that triazole analogs containing long alkyl hydroxyl groups and phenyl groups typically are effective in forming supramolecular gels.
Keywords	alkynes ; azides ; copper ; cycloaddition reactions ; gels ; glucose ; moieties ; molecular weight ; triazoles
Language	English
Dates of publication	2015-0101
Size	p. 82-85.
Publishing place	Elsevier Ltd
Document type	Article
ZDB-ID	204287-3
ISSN	1873-3581 ; 0040-4039
ISSN (online)	1873-3581
ISSN	0040-4039
DOI	10.1016/j.tetlet.2014.11.013
Database	NAL-Catalogue (AGRICOLA)

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Article: Synthesis and study of N-acetyl d-glucosamine triazole derivatives as effective low molecular weight gelators

Mangunuru, Hari P.R / Jayasudhan Reddy Yerabolu / Guijun Wang

Tetrahedron letters. 2015 June 03, v. 56

2015

Abstract: Sugar based low molecular weight gelators have many potential uses for the formation of advanced soft materials. Here we have synthesized a series of peracetylated d-glucosamine triazole derivatives via the Cu catalyzed azide/alkyne cycloaddition ... ...

Abstract	Sugar based low molecular weight gelators have many potential uses for the formation of advanced soft materials. Here we have synthesized a series of peracetylated d-glucosamine triazole derivatives via the Cu catalyzed azide/alkyne cycloaddition reaction (CuAAc) and studied their self-assembling properties in several organic solvents, aqueous solutions, and water. Among the sixteen compounds synthesized and studied, many were able to function as organogelators for multiple solvents. Also seven compounds were able to form hydrogels at low concentrations such as 0.2â1.0wt%. These indicate that peracetylated d-glucosamine triazole analogs are effective small molecular gelators.
Keywords	alkynes ; aqueous solutions ; chemical structure ; copper ; cycloaddition reactions ; glucosamine ; hydrogels ; molecular weight ; solvents ; triazoles
Language	English
Dates of publication	2015-0603
Size	p. 3361-3364.
Publishing place	Elsevier Ltd
Document type	Article
ZDB-ID	204287-3
ISSN	1873-3581 ; 0040-4039
ISSN (online)	1873-3581
ISSN	0040-4039
DOI	10.1016/j.tetlet.2015.02.123
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Article ; Online: Preparation and self-assembly study of amphiphilic and bispolar diacetylene-containing glycolipids.

Wang, Guijun / Goyal, Navneet / Mangunuru, Hari P R / Yang, Hao / Cheuk, Sherwin / Reddy, Puram V Narasimha

The Journal of organic chemistry

2015 Volume 80, Issue 2, Page(s) 733–743

Abstract: Diacetylene-containing glycolipids are a unique class of compounds that are able to self-assemble and form ordered supramolecular structures. Polymerizable diacetylene glycolipids that can function as low molecular weight gelators are particularly ... ...

Abstract	Diacetylene-containing glycolipids are a unique class of compounds that are able to self-assemble and form ordered supramolecular structures. Polymerizable diacetylene glycolipids that can function as low molecular weight gelators are particularly interesting molecules which can lead to stimuli-responsive smart materials. To discover efficient organogelators with built-in functionality that may be useful in sensing local environmental changes, we have synthesized a series of novel diacetylene-containing amide and urea derivatives using D-glucosamine as the starting material. Both amphiphilic and dipolar glycolipids were synthesized, and these compounds are effective gelators for several organic solvents and aqueous solutions. The resulting gels can be cross-linked under 6 W UV light to produce blue or purple polydiacetylene gels. The cross-linked gels obtained from urea derivatives are generally dark blue and exhibit blue to red color transitions upon heating. Compared to the urea derivatives, the analogous diacetylene amides produced blue to deep purple polymerized gels, depending on the structures of the gelators. The morphologies of the gels were characterized by optical microscopy and scanning electron microscopy. Typically, self-assembled fibrous networks were observed. The synthesis and characterization of these polymerizable gelators and their UV-vis absorption upon polymerization are reported.
Language	English
Publishing date	2015-01-16
Publishing country	United States
Document type	Journal Article
ZDB-ID	123490-0
ISSN	1520-6904 ; 0022-3263
ISSN (online)	1520-6904
ISSN	0022-3263
DOI	10.1021/jo501568u
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Article ; Online: Design and Discovery of Water-Soluble Benzooxaphosphole-Based Ligands for Hindered Suzuki-Miyaura Coupling Reactions with Low Catalyst Load.

Shada, Arun D R / Mangunuru, Hari P R / Terrab, Leila / Tenneti, Srinivasarao / Kalikinidi, Nageswara Rao / Naini, Santhosh Reddy / Gajula, Praveen / Crull, Emily B / Janganati, Venumadhav / Kovvuri, Raghavendra / Natarajan, Vasudevan / Lee, Daniel / Yin, Jinya / Samankumara, Lalith / Mahar, Rohit / Zhang, Xueyi / Chen, Anji / Hewa-Rahinduwage, Chathuranga C / Wang, Zhirui /

Mamunooru, Manasa / Rana, Jagruti / Wannere, Chaitanya S / Armstrong, Joseph D / Williamson, R Thomas / Sirasani, Gopal / Qu, Bo / Senanayake, Chris H

Organic letters

2023 Volume 26, Issue 14, Page(s) 2751–2757

Abstract: We report a new class of highly effective, benzooxaphosphole-based, water-soluble ligands in the application of Suzuki-Miyaura cross-coupling reactions for sterically hindered substrates in aqueous media. The catalytic activities of the coupling ... ...

Abstract	We report a new class of highly effective, benzooxaphosphole-based, water-soluble ligands in the application of Suzuki-Miyaura cross-coupling reactions for sterically hindered substrates in aqueous media. The catalytic activities of the coupling reactions were greatly enhanced by the addition of catalytic amounts of organic phase transfer reagents, such as tetraglyme and tetrabutylammonium bromide. The optimized general protocol can be conducted with a low catalyst load, thereby providing a practical solution for these reactions. The viability of this new Suzuki-Miyaura protocol was demonstrated with various substrates to generate important building blocks, including heterocycles, for the synthesis of biologically active compounds.
Language	English
Publishing date	2023-07-24
Publishing country	United States
Document type	Journal Article
ISSN	1523-7052
ISSN (online)	1523-7052
DOI	10.1021/acs.orglett.3c01663
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Article: Preparation and Self-Assembly Study of Amphiphilic and Bispolar Diacetylene-Containing Glycolipids

Wang, Guijun / Cheuk Sherwin / Goyal Navneet / Mangunuru Hari P. R / Reddy Puram V. Narasimha / Yang Hao

Journal of organic chemistry. 2015 Jan. 16, v. 80, no. 2

2015

Abstract	Diacetylene-containing glycolipids are a unique class of compounds that are able to self-assemble and form ordered supramolecular structures. Polymerizable diacetylene glycolipids that can function as low molecular weight gelators are particularly interesting molecules which can lead to stimuli-responsive smart materials. To discover efficient organogelators with built-in functionality that may be useful in sensing local environmental changes, we have synthesized a series of novel diacetylene-containing amide and urea derivatives using d-glucosamine as the starting material. Both amphiphilic and dipolar glycolipids were synthesized, and these compounds are effective gelators for several organic solvents and aqueous solutions. The resulting gels can be cross-linked under 6 W UV light to produce blue or purple polydiacetylene gels. The cross-linked gels obtained from urea derivatives are generally dark blue and exhibit blue to red color transitions upon heating. Compared to the urea derivatives, the analogous diacetylene amides produced blue to deep purple polymerized gels, depending on the structures of the gelators. The morphologies of the gels were characterized by optical microscopy and scanning electron microscopy. Typically, self-assembled fibrous networks were observed. The synthesis and characterization of these polymerizable gelators and their UVâvis absorption upon polymerization are reported.
Keywords	aqueous solutions ; color ; crosslinking ; gels ; glucosamine ; glycolipids ; light microscopy ; molecular weight ; organic chemistry ; polymerization ; scanning electron microscopy ; solvents ; surfactants ; ultraviolet radiation ; ultraviolet-visible spectroscopy ; urea
Language	English
Dates of publication	2015-0116
Size	p. 733-743.
Publishing place	American Chemical Society
Document type	Article
ZDB-ID	123490-0
ISSN	1520-6904 ; 0022-3263
ISSN (online)	1520-6904
ISSN	0022-3263
DOI	10.1021%2Fjo501568u
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Article: Synthesis and characterization of pH responsive D-glucosamine based molecular gelators.

Goyal, Navneet / Mangunuru, Hari P R / Parikh, Bargav / Shrestha, Sonu / Wang, Guijun

Beilstein journal of organic chemistry

2014 Volume 10, Page(s) 3111–3121

Abstract: Small molecular gelators are a class of compounds with potential applications for soft biomaterials. Low molecular weight hydrogelators are especially useful for exploring biomedical applications. Previously, we found that 4,6-O-benzylidene acetal ... ...

Abstract	Small molecular gelators are a class of compounds with potential applications for soft biomaterials. Low molecular weight hydrogelators are especially useful for exploring biomedical applications. Previously, we found that 4,6-O-benzylidene acetal protected D-glucose and D-glucosamine are well-suited as building blocks for the construction of low molecular weight gelators. To better understand the scope of D-glucosamine derivatives as gelators, we synthesized and screened a novel class of N-acetylglucosamine derivatives with a p-methoxybenzylidene acetal protective group. This modification did not exert a negative influence on the gelation. On the contrary, it actually enhanced the gelation tendency for many derivatives. The introduction of the additional methoxy group on the phenyl ring led to low molecular weight gelators with a higher pH responsiveness. The resulting gels were stable at neutral pH values but degraded in an acidic environment. The release profiles of naproxen from the pH responsive gels were also analyzed under acidic and neutral conditions. Our findings are useful for the design of novel triggered release self-assembling systems and can provide an insight into the influence of the the structure on gelation.
Language	English
Publishing date	2014-12-23
Publishing country	Germany
Document type	Journal Article
ZDB-ID	2192461-2
ISSN	1860-5397
ISSN	1860-5397
DOI	10.3762/bjoc.10.328
Database	MEDical Literature Analysis and Retrieval System OnLINE

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