Tag: 300-400

New Synthetic Technologies for the Construction of Heterocycles and Tryptamines was written by Nicolaou, K. C.;Krasovskiy, Arkady;Majumder, Utpal;Trepanier, Vincent E.;Chen, David Y.-K.. And the article was included in Journal of the American Chemical Society in 2009.Category: indole-building-block The following contents are mentioned in the article:

New synthetic methods for the construction of novel heterocycles and tryptamines are described. Thus, N-Boc anilines are sequentially converted to (3-(2-aminophenyl)pyrrolidin-3-ol) derivatives, substituted 2-oxo-1,2-dihydrospirobenzo[d][1,3]oxazine-4,3′-pyrrolidines, and 2-(4,5-dihydro-1H-pyrrol-3-yl)aniline derivatives through a route involving t-BuLi induced ortho-metalation/LaCl₃·2LiCl metal exchange, reaction with N-Boc pyrrolidin-3-one, and subsequent decarboxylative fragmentation. Labile intermediates 2-(4,5-dihydro-1H-pyrrol-3-yl)anilines are effectively converted to tryptamines under controlled protic acid conditions. In addition to providing expedient access to the 2-oxo-1,2-dihydrospirobenzo[d][1,3]oxazine-4,3′-pyrrolidines, the method is applicable to the synthesis of the corresponding 2-oxo-1,2-dihydrospirobenzo[d][1,3]oxazine-4,3′-piperidine series of spirocycles and their precursors 3-(2-aminophenyl)piperidin-3-ol derivatives by using N-Boc-protected piperidin-3-one. Applications of the developed synthetic technologies to the synthesis of regioisomeric spirocycles, tryptamines, Corey’s aspidophytine tryptamine, and efavirenz are also described. This study involved multiple reactions and reactants, such as tert-Butyl (2-(5-(trifluoromethyl)-1H-indol-3-yl)ethyl)carbamate (cas: 1132910-79-2Category: indole-building-block).

tert-Butyl (2-(5-(trifluoromethyl)-1H-indol-3-yl)ethyl)carbamate (cas: 1132910-79-2) belongs to indole derivatives. Indole produced by Proteus, Pseudomonas, Escherichia and other species was shown to be a growth promoting factor in Arabidopsis thaliana.Indole was synthesized in moderate yield via an o-naphthoquinone catalyzed tandem cross-coupling of substituted aniline and benzylamine under aerobic oxidation conditions.Category: indole-building-block

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Application of a spin-labeled spin-trap to the detection of nitric oxide (NO) was written by Marx, Lucien;Rassat, Andre. And the article was included in Angewandte Chemie, International Edition in 2000.Safety of 2-Benzyl-5-bromoisoindoline-1,3-dione The following contents are mentioned in the article:

We suggest a new use of diradicals as spin-labeled spin-traps. These reagents would combine a stable radical (R_T), designed to trap selectively the radical to be detected and to yield diamagnetic products, and another radical (R_L), unreactive during this reaction, at a distance such that the diradical EPR spectrum would be a single line. In this way, as R_T reacts, the signal of the R_T moiety would be detected at the very beginning of the reaction, with both the concentration of spin trap and of spin adduct being monitored on the same spectrum. Furthermore, the rate of the trapping reaction (usually bimol.) could easily be increased by increasing the biradical concentration As an example of this method, we have studied the trapping of NO by a new diradical that was designed to combine two aminoxy groups on an isoindoline backbone. The diradical was prepared in six steps from phthalic anhydride. When nitric oxide was bubbled into a deoxygenated solution of the synthesized aminoxy-isoindoline derivative in ethanol, samples were taken after 10,30, 60, and 90 min and analyzed by thin layer chromatog. and EPR; a three-line spectrum, not apparent in the spectrum of the sample taken after 10 min, appeared superimposed on the diradical spectrum of the sample taken after 30 min. Four new nitroxides were then detected : they all displayed the same typical isoindolidinyloxyl(radical) 3-line EPR spectrum (toluene, a_N = 1.37 mT). This study involved multiple reactions and reactants, such as 2-Benzyl-5-bromoisoindoline-1,3-dione (cas: 82104-06-1Safety of 2-Benzyl-5-bromoisoindoline-1,3-dione).

2-Benzyl-5-bromoisoindoline-1,3-dione (cas: 82104-06-1) belongs to indole derivatives. Indole produced by Proteus, Pseudomonas, Escherichia and other species was shown to be a growth promoting factor in Arabidopsis thaliana. It is used in perfumery and in making tryptophan, an essential amino acid, and indoleacetic acid (heteroauxin), a hormone that promotes the development of roots in plant cuttings.Safety of 2-Benzyl-5-bromoisoindoline-1,3-dione

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Potent non-hydroxamate inhibitors of histone deacetylase-8: Role and scope of an isoindolin-2-yl linker with an α-amino amide as the zinc-binding unit was written by Greenwood, Simon O. R.;Chan, A. W. Edith;Hansen, D. Flemming;Marson, Charles M.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2020.Safety of 2-Benzyl-5-bromoisoindoline-1,3-dione The following contents are mentioned in the article:

A series of potent inhibitors of histone deacetylase-8 (HDAC8) is described that contains an α-amino amide zinc-binding unit and a substituted isoindolinyl capping group. The presence of a 2,4-dichlorophenyl unit located in the acetate-release cavity was shown to confer a gain of approx. 4.3 kJ mol^-1 in binding energy compared to a Ph group, and the isoindoline linker has approx. 5.8 kJ mol^-1 greater binding energy than the corresponding tetrahydroisoquinoline ring system. In a series of 5-substituted isoindolin-2-yl inhibitors, a 5-acetylamino derivative was found to be more potent than the 5-unsubstituted lead HDAC8 inhibitor (increase in binding energy of 2.0 kJ mol^-1, ascribed to addnl. binding interactions within the N_ε-acetyl-L-lysine binding tunnel in HDAC8, including hydrogen bonding to Asp101. Tolerance of a 5-substituent (capping group) on the isoindoline ring has been demonstrated, and which in some cases confers improved enzyme inhibition, the HDAC8 substrate-binding region providing a platform for addnl. interactions. This study involved multiple reactions and reactants, such as 2-Benzyl-5-bromoisoindoline-1,3-dione (cas: 82104-06-1Safety of 2-Benzyl-5-bromoisoindoline-1,3-dione).

2-Benzyl-5-bromoisoindoline-1,3-dione (cas: 82104-06-1) belongs to indole derivatives. The indole subunit is an almost ubiquitous component of biologically active natural products, and its study has been the focus of research for decades. It is used in perfumery and in making tryptophan, an essential amino acid, and indoleacetic acid (heteroauxin), a hormone that promotes the development of roots in plant cuttings.Safety of 2-Benzyl-5-bromoisoindoline-1,3-dione

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

On January 15, 2004, Seeberger, Peter H.; Hewitt, Michael C.; Snyder, Daniel published a patent.Formula: C16H19NO6S The title of the patent was Solid-phase and solution-phase synthesis of glycosylphosphatidylinositol glycans. And the patent contained the following:

One aspect of the present invention relates to solution-phase synthesis approaches to glycosylphosphatidylinositol (GPI) I, wherein, n is 1-4; R represents independently for each occurrence H, alkyl, aryl, CH2-aryl, C(O)-alkyl, C(O)-aryl, or Si(alkyl)3; R1 and R2 are independently H, CH2-aryl, C(O)-alkyl, C(O)-aryl, Si(alkyl)3; or R1 and R2 taken together are C(CH3)2, P(O)OH, or P(O)OR5; R3 is amino, N3, or NH3X; R4 represents independently for each occurrence H, alkyl, aryl, CH2-aryl, C(O)- alkyl, C(O)-aryl, Si(alkyl)3, or P(O)(OR5)2; R5 represents independently for each occurrence H, Li+, Na+, K+, Rb+, Cs+, aryl, or an optionally substituted alkyl group; and X is a halogen, alkyl carboxylate, or aryl carboxylate. Another aspect of the present invention relates to key building blocks, and syntheses thereof, useful for GPI assembly. Yet another aspect of the invention relates to an automated method for the synthesis of GPIs and fragments thereof. The synthesis of a pseudo-hexasaccharide glycosylphosphatidylinositol has been reduced to practice, both in solution and using a combination of solution and automated solid-phase methodologies. The material made in solution was covalently attached to a protein carrier and used to vaccinate mice. Inoculated mice were substantially protected against a subsequent challenge with Plasminodium parasites. This discovery further implicates GPI as the dominant toxin in malaria infections, and lays the groundwork for future trials in human volunteers. Combinations of solution and automated solid-phase synthetic methodologies will see continued usage in this context, and are expected to lead to the rapid generation of more potent vaccines for malaria and other maladies. The experimental process involved the reaction of Ethyl 2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-thio-beta-D-glucopyranoside(cas: 130539-43-4).Formula: C16H19NO6S

The Article related to glycosylphosphatidylinositol oligosaccharide glycan solid phase synthesis vaccine human, Carbohydrates: Alditols, Cyclitols, Glycerides and other aspects.Formula: C16H19NO6S

Referemce:
Indole alkaloid derivatives as building blocks of natural products from聽Bacillus thuringiensis聽and聽Bacillus velezensis聽and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

On March 31, 2003, Sarkar, Kakali; Mukherjee, Indrani; Roy, Nirmolendu published an article.Computed Properties of 130539-43-4 The title of the article was Synthesis of the trisaccharide repeating unit of the O-antigen related to the enterohemorrhagic Escherichia coli type O26:H. And the article contained the following:

L-Fucose was converted to the 2-azido-2-deoxy-L-fucose derivative, which together with the monosaccharide synthons prepared from L-rhamnose and D-glucosamine hydrochloride were utilized for the synthesis of the p-ethoxyphenyl glycoside of the trisaccharide repeating unit of the antigen from enterohemorrhagic Escherichia coli type O26:H. The experimental process involved the reaction of Ethyl 2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-thio-beta-D-glucopyranoside(cas: 130539-43-4).Computed Properties of 130539-43-4

The Article related to fucopyranosyl glucopyranosyl rhamnopyranoside trisaccharide synthesis repeating unit escherichia coli, trisaccharide repeating unit synthesis antigen escherichia coli, Carbohydrates: Amines and other aspects.Computed Properties of 130539-43-4

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

On August 31, 2005, Sundgren, Andreas; Lahmann, Martina; Oscarson, Stefan published an article.Formula: C16H19NO6S The title of the article was Block synthesis of Streptococcus pneumoniae type 14 capsular polysaccharide structures. And the article contained the following:

Synthesis of a thioglycoside tetrasaccharide block, β-D-Galp-(1â†?)-β-DGlcp-(1â†?)-[β-D-Galp-(1â†?)]-β-D-GlcNPhthp-(1→SEt), corresponding to the repeating unit of Streptococcus pneumoniae serotype 14 CPS is described. Coupling of this block with a spacer followed by removal of an isopropylidene acetal yielded an acceptor, which was elongated with the donor block to give a protected dimer of the repeating unit. Iteration of this methodol. yielded the trimer. Deprotection then produced an octa and a dodecasaccharide derivative ready for conjugation to proteins to afford immunoactive glycoconjugates. The experimental process involved the reaction of Ethyl 2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-thio-beta-D-glucopyranoside(cas: 130539-43-4).Formula: C16H19NO6S

The Article related to capsular polysaccharide preparation streptococcus pneumoniae, Carbohydrates: Amines and other aspects.Formula: C16H19NO6S

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Li, Wei; Gao, Yu; Li, Qing; Li, Zhong-Jun published an article in 2018, the title of the article was Ionic-liquid supported rapid synthesis of an N-glycan core pentasaccharide on a 10 g scale.Quality Control of Ethyl 2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-thio-beta-D-glucopyranoside And the article contains the following content:

A new and efficient Ionic Liquid-Supported Oligosaccharide Synthesis (ILSOS) strategy for an N-linked core pentasaccharide on a 10 g scale is reported. This new ILSOS includes a new spacer for an IL support, a new tagging strategy, and fast, efficient and orthogonal removal of the ionic-liquid support, producing the N-linked core pentasaccharide with direct applicability potential in a short time, with high yield and on a large gram scale. The experimental process involved the reaction of Ethyl 2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-thio-beta-D-glucopyranoside(cas: 130539-43-4).Quality Control of Ethyl 2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-thio-beta-D-glucopyranoside

The Article related to glycan pentasaccharide ionic liquid supported synthesis orthogonal protecting group, Carbohydrates: Amines and other aspects.Quality Control of Ethyl 2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-thio-beta-D-glucopyranoside

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

On June 13, 2008, Minuth, Tobias; Boysen, Mike M. K. published an article.Product Details of 130539-43-4 The title of the article was A general and efficient route to 3-O-modified carbohydrate bis(oxazoline) ligands. And the article contained the following:

An efficient route to derivatives of carbohydrate-based bis(oxazoline) ligands with 3-O substituents of varying steric demand is described. The synthesis of the new ligands proceeds via a thioglucoside key intermediate. The double cyclization to the desired bis(oxazolines) is initiated with N-iodosuccinimide under mild conditions. Employing this strategy, four new 3-O-modified bis(oxazoline) ligands were obtained in good yields. The experimental process involved the reaction of Ethyl 2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-thio-beta-D-glucopyranoside(cas: 130539-43-4).Product Details of 130539-43-4

The Article related to thioglucoside malonamide cyclization, glucosamine oxazoline chiral ligand asym synthesis, Carbohydrates: Amines and other aspects.Product Details of 130539-43-4

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

On August 31, 2006, Gening, M. L.; Tsvetkov, Yu. E.; Pier, G. B.; Nifantiev, N. E. published an article.Application of 130539-43-4 The title of the article was The study of the reaction of terminated oligomerization in the synthesis of oligo-(β1-6)-glucosamines. And the article contained the following:

The applicability of terminated oligomerization to the synthesis of oligo-(β1-6)-glucosamines, fragments of the intercellular polysaccharide adhesion of staphylococci, was studied. The reactions of terminated oligomerization were carried out with mono-, di-, and trisaccharide monomers and N-protected aminopropanol; and mono- and disaccharides as terminating mols. were also attempted. The primary formation of cyclic products of monomer intramol. glycosylation was observed in almost all the reactions. Only the experiments with the monomer based on the disaccharide bromide under the conditions of the Helferich reaction led to reduced yields (30%) of the cyclic products. However, even in this case, the desired terminated oligosaccharides were generated in approx. 10% yield and mainly were the products of single glycosylation of the terminator by the monomer. These experiments allow the conclusion that, under the examined conditions, the reaction of terminated oligomerization could not result in the synthesis of oligo-glucosamines with a high mol. mass. The experimental process involved the reaction of Ethyl 2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-thio-beta-D-glucopyranoside(cas: 130539-43-4).Application of 130539-43-4

The Article related to disaccharide trisaccharide oligosaccharide oligomerization glycosylation preparation glucosamine, Carbohydrates: Amines and other aspects.Application of 130539-43-4

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

On July 2, 2010, Kamkhachorn, Teerada; Parameswar, Archana R.; Demchenko, Alexei V. published an article.Category: indole-building-block The title of the article was Comparison of the Armed/Disarmed Building Blocks of the D-Gluco and D-Glucosamino Series in the Context of Chemoselective Oligosaccharide Synthesis. And the article contained the following:

A very elegant Fraser-Reid armed-disarmed approach recently expanded to the building blocks of the superarmed and superdisarmed series shows very high utility in chemoselective oligosaccharide synthesis. Although a number of studies dedicated to the chemoselective activation of 2-amino-2-deoxysugars have emerged, little remains known about how the reactivity of the armed/disarmed building blocks of the neutral sugars directly compares to that of their 2-aminosugar counterparts. A preliminary study of this comparative reactivity is presented. The experimental process involved the reaction of Ethyl 2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-thio-beta-D-glucopyranoside(cas: 130539-43-4).Category: indole-building-block

The Article related to oligosaccharide chemoselective synthesis, fraser reid armed disarmed glycosylation amino deoxysugar, Carbohydrates: Amines and other aspects.Category: indole-building-block

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles