Heterocyclic Building Blocks-Thiazolidine

Stereoselective and Catalytic Synthesis of anti-β-Alkoxy-α-azido Carboxylic Derivatives was written by Fernandez-Valparis, Javier;Romea, Pedro;Urpi, Felix;Font-Bardia, Merce. And the article was included in Organic Letters in 2017.Recommanded Product: 76186-04-4 This article mentions the following:

Nonracemic azidoacetyl thiazolidinethione I was prepared; in the presence of NiCl₂(PMe₃)₂, I underwent diastereoselective condensation reactions with aryl aldehyde acetals RCH(OR¹)₂ (R = 4-MeOC₆H₄, 3-MeOC₆H₄, 2-MeOC₆H₄, 1,3-benzodioxol-5-yl, 4-Me₂NC₆H₄, 4-MeC₆H₄, Ph, 4-ClC₆H₄; R¹ = Me, H₂C:CHCH₂, PhCH₂) and alkynyl dicobalt hexacarbonyl complexes mediated by Et₃SiOTf and 2,6-lutidine in CH₂Cl₂ to yield nonracemic β-alkoxy-β-aryl-α-azidopropanoyl thiazolidinethiones such as II (R = 4-MeOC₆H₄, 3-MeOC₆H₄, 2-MeOC₆H₄, 1,3-benzodioxol-5-yl, 4-Me₂NC₆H₄, 4-MeC₆H₄, Ph, 4-ClC₆H₄; R¹ = Me, H₂C:CHCH₂, PhCH₂) and dicobalt hexacarbonyl β-alkoxy-α-azidobutynoyl thiazolidinethiones in 15-85% yields (three of eighteen examples < 50% yields) and in 60:40->97:3 dr (three of eighteen examples < 80:20 dr). In the experiment, the researchers used many compounds, for example, (S)-4-Isopropylthiazolidine-2-thione (cas: 76186-04-4Recommanded Product: 76186-04-4).

(S)-4-Isopropylthiazolidine-2-thione (cas: 76186-04-4) belongs to thiazolidine derivatives. Thiazolidine motifs are very intriguing heterocyclic five-membered moieties present in diverse natural and bioactive compounds having sulfur at the first position and nitrogen at the third position. In addition, the use of thiazolidines as an inhibitor of tyrosyl-DNA phosphodiesterase Iand influenza neuraminidase, pro-drugs for the treatment of cystinosis, radioprotective against γ-irradiation and as S1P1 receptor agonist has also been reported.Recommanded Product: 76186-04-4

Referemce:
Thiazolidine – Wikipedia,
Thiazolidine – ScienceDirect.com

A rational eco-compatible design strategy for regio- and diastereoselective synthesis of novel dispiropyrrolidine/thiapyrrolizidine hybrids was written by Dandia, Anshu;Singh, Ruby;Khan, Shahnawaz;Kumari, Sukhbeer;Soni, Pragya. And the article was included in Tetrahedron Letters in 2015.Application In Synthesis of Thiazolidine-4-carboxylic acid This article mentions the following:

A facile regio- and stereoselective synthesis of novel dispiroheterocyclic hybrids containing benzo[1,4]oxazine/benzo[1,4]thiazine and pyrrolidine/thiapyrrolizidine moieties via 1,3-dipolar cycloaddition reaction was carried out. The reaction has been carried out using 2,2,2-trifluoroethanol as a new alternative green solvent and catalyst for rapid access to construct a diversity-oriented library of regioselective dispiropyrrolidine/thiapyrrolizidines. Mild reaction conditions with excellent conversion, higher yields in shorter reaction times and the easy recyclability of 2,2,2-trifluoroethanol makes this protocol attractive, sustainable and environmentally benign. In the experiment, the researchers used many compounds, for example, Thiazolidine-4-carboxylic acid (cas: 444-27-9Application In Synthesis of Thiazolidine-4-carboxylic acid).

Thiazolidine-4-carboxylic acid (cas: 444-27-9) belongs to thiazolidine derivatives. Thiazolidine is a heterocyclic compound with five-membered saturated ring with a thioether group and an amine group in 1 and 3 positions of the ring. Thiazolidine and its composites are key components of many natural products and drugs , and are also present in many synthetic compounds such as anticancer, anti-inflammatory, antitubercular, antifungal, antiviral, anti-HIV, cytotoxicity, antitrypanosomal, antinociceptive and anti-hypernociceptive compounds.Application In Synthesis of Thiazolidine-4-carboxylic acid

Referemce:
Thiazolidine – Wikipedia,
Thiazolidine – ScienceDirect.com

Heptafluorobutyl chloroformate-based sample preparation protocol for nonchiral and chiral amino acid analysis by gas chromatography-mass spectrometry was written by Simek, Petr;Husek, Petr;Zahradnickova, Helena. And the article was included in Methods in Molecular Biology (New York, NY, United States) in 2019.Quality Control of Thiazolidine-4-carboxylic acid This article mentions the following:

Gas chromatog. (GC) is a commonly used technique in amino acid anal. (AAA). However, one of the requirements of the application of GC for AAA is a need for the polar analytes to be converted into their volatile, thermally stable derivatives In the last two decades, alkyl chloroformates (RCFs) have become attractive derivatization reagents. The reagents react immediately with most amino acid functional groups in aqueous matrixes, and the process can easily be coupled with liquid-liquid extraction of the resulting less polar derivatives into immiscible organic phase. Here we describe a simple protocol for in situ derivatization of amino acids with heptafluorobutyl chloroformate (HFBCF) followed by subsequent chiral as well as nonchiral GC/MS (mass spectrometric) anal. on a resp. nonpolar fused silica and an enantioselective Chirasil-Val capillary column. In the experiment, the researchers used many compounds, for example, Thiazolidine-4-carboxylic acid (cas: 444-27-9Quality Control of Thiazolidine-4-carboxylic acid).

Thiazolidine-4-carboxylic acid (cas: 444-27-9) belongs to thiazolidine derivatives. Thiazolidine is a heterocyclic compound with five-membered saturated ring with a thioether group and an amine group in 1 and 3 positions of the ring. Thiazolidine is prepared as it was in its first reported synthesis, by the condensation of cysteamine and formaldehyde. Other thiazolidines may be synthesized by similar condensations. A notable derivative is 4-carboxythiazolidine, derived from formaldehyde and cysteine.Quality Control of Thiazolidine-4-carboxylic acid

Referemce:
Thiazolidine – Wikipedia,
Thiazolidine – ScienceDirect.com

A Larock indolization approach to substituted tryptamines was written by Moss, Thomas A.;Lister, Andrew S.;Wang, Jimmy. And the article was included in Tetrahedron Letters in 2017.COA of Formula: C8H15NO5S This article mentions the following:

Substituted tryptamines, an important class of heterocycle in both natural products and medicinal chem., are readily accessible through a Larock indolization approach. The acetylene precursors are in turn routinely accessed as single enantiomers from ring opening of chiral cyclic sulfamidate precursors. Using this two-step protocol, a range of unnatural substituted tryptamines have been synthesized in good yields. In the experiment, the researchers used many compounds, for example, (R)-3-Boc-4-methyl-1,2,3-oxathiazolidine 2,2-Dioxide (cas: 454248-53-4COA of Formula: C8H15NO5S).

(R)-3-Boc-4-methyl-1,2,3-oxathiazolidine 2,2-Dioxide (cas: 454248-53-4) belongs to thiazolidine derivatives. Thiazolidine is a heterocyclic compound with five-membered saturated ring with a thioether group and an amine group in 1 and 3 positions of the ring. In addition, the use of thiazolidines as an inhibitor of tyrosyl-DNA phosphodiesterase Iand influenza neuraminidase, pro-drugs for the treatment of cystinosis, radioprotective against γ-irradiation and as S1P1 receptor agonist has also been reported.COA of Formula: C8H15NO5S

Referemce:
Thiazolidine – Wikipedia,
Thiazolidine – ScienceDirect.com

Oxidation of β-DL-thiaproline, a possible natural substrate of D-amino acid oxidase was written by Foppoli, C.;Cini, C.;Blarzino, C.;De Marco, C.. And the article was included in Italian Journal of Biochemistry in 1981.Product Details of 16310-13-7 This article mentions the following:

The ability of D-amino acid oxidase to oxidize the proline analog, β-DL-thiaproline (I), was tested. O₂ consumption rates with I or D-proline as substrate were determined at several pH values and substrate concentrations I was fully oxidizable, with a K_m of 3.1 mM at pH 7.4, and V_max of 6.6 μL O₂/min, compared to K_m and V_max values for D-proline of 2.3 mM and 5.8 μL O₂/min, resp. At pH 8.3, K_m values for D-proline and I were 1.9 and 2.1 mM, resp., and V_max 6.2 and 3.4 μL O₂/min. The product of I oxidation was Δ²-thiazoline 2-carboxylic acid (II), which was hydrolyzed to N-oxalylcysteamine in acidic solutions Thus, I, produced in vivo from cysteamine and glyoxylate, may be a physiol. substrate for D-amino acid oxidase. In the experiment, the researchers used many compounds, for example, Thiazolidine-2-carboxylic acid (cas: 16310-13-7Product Details of 16310-13-7).

Thiazolidine-2-carboxylic acid (cas: 16310-13-7) belongs to thiazolidine derivatives. Derivatives, thiazolidines, are known. For example, the drug pioglitazone contains a thiazolidine ring. Another drug that contains a thiazolidine ring is the antibiotic penicillin. Thiazolidine-2,4-dione (TZD) is an important derivative of thiazolidine with a sulfur and nitrogen atom in positions 1 and 3, and carbonyl in position 4 of the ring. These derivatives have a wide range of medicinal applications such as antiviral, antimicrobial, anticonvulsant, antiinflammatory, and antimalarial activities.Product Details of 16310-13-7

Referemce:
Thiazolidine – Wikipedia,
Thiazolidine – ScienceDirect.com

Impurity profiling of N,N’-ethylenebis-L-cysteine diethyl ester (Bicisate) was written by Wahl, Oliver;Cleynhens, Jan;Verbruggen, Alfons M.;Holzgrabe, Ulrike. And the article was included in Journal of Pharmaceutical and Biomedical Analysis in 2018.Reference of 444-27-9 This article mentions the following:

A HPLC-UV-CAD method with a HILIC column for impurity profiling of the ⁹⁹Tc chelating agent bicisate has been developed and evaluated. Bicisate and its impurities were separated by means of isocratic elution on a zwitterionic stationary phase using a mixture of 7.5 mmol/L trifluoroacetic acid and acetonitrile (47.5:52.5 V/V) as the mobile phase. Five different bicisate batches of a manufacturer were tested using the method. In addition LC-MS experiments were conducted in order to identify the impurities. The predominant impurities found were the oxidation product (disulfide), the monoester of ethylene dicysteine and an unknown compound with an m/z of 293 in ESI pos. mode. A new degradation product of bicisate, bicisate lactam, was identified during sample solution stability assessment. In the experiment, the researchers used many compounds, for example, Thiazolidine-4-carboxylic acid (cas: 444-27-9Reference of 444-27-9).

Thiazolidine-4-carboxylic acid (cas: 444-27-9) belongs to thiazolidine derivatives. Derivatives, thiazolidines, are known. For example, the drug pioglitazone contains a thiazolidine ring. Another drug that contains a thiazolidine ring is the antibiotic penicillin. Thiazolidines have been applied as prodrug derivatives for various steroids containing a 3-carbonyl group to improve their topical anti-inflammatory activity. Reference of 444-27-9

Referemce:
Thiazolidine – Wikipedia,
Thiazolidine – ScienceDirect.com

New general asymmetric synthesis of versatile γ-alkylated butenolides and its application to expeditious synthesis of the chiral Geissman-Waiss lactones useful for (+)-retronecine synthesis was written by Nagao, Yoshimitsu;Dai, Wei Min;Ochiai, Masahito;Shiro, Motoo. And the article was included in Journal of Organic Chemistry in 1989.Quality Control of (S)-4-Isopropylthiazolidine-2-thione This article mentions the following:

A new strategy for general asym. synthesis of chiral butenolides, e.g. I, is established by utilizing excellent diastereocontrolled alkylation with chiral tin(II) enolate of II at the γ-position of hydroxy butenolides. An efficient utility of the chiral butenolides is exemplified with the expeditious synthesis of the optically pure Geissman-Waiss lactone derivatives III (R = CO₂Et, CH₂O₂CCMe₃). In the experiment, the researchers used many compounds, for example, (S)-4-Isopropylthiazolidine-2-thione (cas: 76186-04-4Quality Control of (S)-4-Isopropylthiazolidine-2-thione).

(S)-4-Isopropylthiazolidine-2-thione (cas: 76186-04-4) belongs to thiazolidine derivatives. Thiazolidine motifs are very intriguing heterocyclic five-membered moieties present in diverse natural and bioactive compounds having sulfur at the first position and nitrogen at the third position. Thiazolidine is prepared as it was in its first reported synthesis, by the condensation of cysteamine and formaldehyde. Other thiazolidines may be synthesized by similar condensations. A notable derivative is 4-carboxythiazolidine, derived from formaldehyde and cysteine.Quality Control of (S)-4-Isopropylthiazolidine-2-thione

Referemce:
Thiazolidine – Wikipedia,
Thiazolidine – ScienceDirect.com

Radio protective effects of thiazolidines was written by Fatome, M.;Poutrain, P.;Granger, Robert;Orzalesi, Henri;Robbe, Y.;Randon, M.;Fernandez, J. P.. And the article was included in Chimica Therapeutica in 1970.Application In Synthesis of Thiazolidine-2-carboxylic acid This article mentions the following:

In general, the 30 thiazolidines (I) studied were less toxic (LD50 >500 mg/kg, i.p.) than cysteamine (LD50 ∼200 mg/kg) and showed interesting radioprotective activity in mice. The compounds were given i.p. 15 min before irradiation I (R1 = R2 = Me), I (R1 = Me, R2 = Et), I (R1, R2 = cycloheptyl ring), and I (R1 = Ph, R2 = H), the most notable compounds, protected >80% of the mice from death after irradiation with 850 R. I were prepared by the Tsukerman (1956) method. In the experiment, the researchers used many compounds, for example, Thiazolidine-2-carboxylic acid (cas: 16310-13-7Application In Synthesis of Thiazolidine-2-carboxylic acid).

Thiazolidine-2-carboxylic acid (cas: 16310-13-7) belongs to thiazolidine derivatives. Thiazolidines undergo hydrolysis to aldehyde and amino thiol under acid or basic aqueous conditions. In addition, the use of thiazolidines as an inhibitor of tyrosyl-DNA phosphodiesterase Iand influenza neuraminidase, pro-drugs for the treatment of cystinosis, radioprotective against γ-irradiation and as S1P1 receptor agonist has also been reported.Application In Synthesis of Thiazolidine-2-carboxylic acid

Referemce:
Thiazolidine – Wikipedia,
Thiazolidine – ScienceDirect.com

Crystal structures of 6a,6b,7,11a-tetrahydro-6H,9H-spiro[chromeno[3′,4′:3,4]pyrrolo[1,2-c]thiazole-11,3′-indoline]-2′,6-dione and 5′-methyl-6a,6b,7,11a-tetrahydro-6H,9H-spiro[chromeno[3′,4′:3,4]pyrrolo[1,2-c]thiazole-11,3′-indoline]-2′,6-dione was written by Pangajavalli, S.;Ranjithkumar, R.;Srinivasan, N.;Ramaswamy, S.;Selvanayagam, S.. And the article was included in Acta Crystallographica, Section E: Crystallographic Communications in 2019.Name: Thiazolidine-4-carboxylic acid This article mentions the following:

The title compounds, C₂₀H₁₆N₂O₃S, (I), and C₂₁H₁₈N₂O₃S, (II), differ by the presence of a Me group in position 5 on the 1H-indole-2-one ring of compound (II). The two compounds have a structural overlap r.m.s. deviation of 0.48 Å. There is a significant difference in the conformation of the thiazolidine ring: it has a twisted conformation on the fused N-C bond in (I), but an envelope conformation in compound (II) with the S atom as the flap. The planar pyrrolidine ring of the indole ring system is normal to the mean plane of the five-membered pyrrolidine ring of the pyrrolothiazole unit in both compounds, with dihedral angles of 88.71 (9) and 84.59 (8)°. The pyran rings in both structures have envelope conformations with the methylene C atom adjacent to the C=O group as the flap. In both compounds, there is a short intramol. C-H…O contact present. In the crystal of (I), mols. are linked by C-H…O hydrogen bonds forming chains propagating along the b-axis direction. The chains are linked by N-H…π interactions, forming layers parallel to (10 [inline formula omitted]). In the crystal of (II), mols. are linked by pairs of N-H…O hydrogen bonds, forming inversion dimers which are linked by C-H…O hydrogen bonds to form a three-dimensional structure. In the experiment, the researchers used many compounds, for example, Thiazolidine-4-carboxylic acid (cas: 444-27-9Name: Thiazolidine-4-carboxylic acid).

Thiazolidine-4-carboxylic acid (cas: 444-27-9) belongs to thiazolidine derivatives. The thiazolidine ring is a cyclic N,S acetal, and most syntheses of perhydrothiazolo [3,2-a]pyridines construct the five-membered ring by condensation of aldehydes or ketones either as such or masked. In addition, the use of thiazolidines as an inhibitor of tyrosyl-DNA phosphodiesterase Iand influenza neuraminidase, pro-drugs for the treatment of cystinosis, radioprotective against γ-irradiation and as S1P1 receptor agonist has also been reported.Name: Thiazolidine-4-carboxylic acid

Referemce:
Thiazolidine – Wikipedia,
Thiazolidine – ScienceDirect.com

Thiazolidine-Masked α-Oxo Aldehyde Functionality for Peptide and Protein Modification was written by Bi, Xiaobao;Pasunooti, Kalyan Kumar;Lescar, Julien;Liu, Chuan-Fa. And the article was included in Bioconjugate Chemistry in 2017.Name: Thiazolidine-2-carboxylic acid This article mentions the following:

α-Oxo aldehyde-based bioconjugation chem. has been widely explored in peptide and protein modifications for various applications in biomedical research during the past decades. The generation of α-oxo aldehyde via sodium periodate oxidation is usually limited to the N-terminus of a target protein. Internal-site functionalization of proteins with the α-oxo aldehyde handle has not been achieved yet. Herein the authors report a novel method for site-specific peptide and protein modification using synthetically or genetically incorporated thiazolidine-protected α-oxo aldehyde. Efficient unmasking of the aldehyde was achieved by silver ion-mediated hydrolysis of thiazolidine under mild conditions for the first time. A model peptide and a recombinant protein were used to demonstrate the utility of this new method, which were site-specifically modified by oxime ligation with an oxyamine-functionalized peptide labeling reagent. Therefore, the authors’ current method has enriched the α-oxo aldehyde synthetic tool box in peptide and protein bioconjugation chem. and holds great potential to be explored in novel applications in the future. In the experiment, the researchers used many compounds, for example, Thiazolidine-2-carboxylic acid (cas: 16310-13-7Name: Thiazolidine-2-carboxylic acid).

Thiazolidine-2-carboxylic acid (cas: 16310-13-7) belongs to thiazolidine derivatives. Thiazolidine motifs are very intriguing heterocyclic five-membered moieties present in diverse natural and bioactive compounds having sulfur at the first position and nitrogen at the third position. Thiazolidines have been applied as prodrug derivatives for various steroids containing a 3-carbonyl group to improve their topical anti-inflammatory activity. Name: Thiazolidine-2-carboxylic acid

Referemce:
Thiazolidine – Wikipedia,
Thiazolidine – ScienceDirect.com