Tag: 133.1689

Thioproline formation as a driver of formaldehyde toxicity in Escherichia coli was written by Patterson, Jenelle A.;He, Hai;Folz, Jacob S.;Li, Qiang;Wilson, Mark A.;Fiehn, Oliver;Bruner, Steven D.;Bar-Even, Arren;Hanson, Andrew D.. And the article was included in Biochemical Journal in 2020.Synthetic Route of C4H7NO2S This article mentions the following:

Formaldehyde (HCHO) is a reactive carbonyl compound that formylates and cross-links proteins, DNA, and small mols. It is of specific concern as a toxic intermediate in the design of engineered pathways involving methanol oxidation or formate reduction The interest in engineering these pathways is not, however, matched by engineering-relevant information on precisely why HCHO is toxic or on what damage-control mechanisms cells deploy to manage HCHO toxicity. The only well-defined mechanism for managing HCHO toxicity is formaldehyde dehydrogenase-mediated oxidation to formate, which is counterproductive if HCHO is a desired pathway intermediate. We therefore sought alternative HCHO damage-control mechanisms via comparative genomic anal. This anal. associated homologs of the Escherichia coli pepP gene with HCHO-related one-carbon metabolism Furthermore, deleting pepP increased the sensitivity of E. coli to supplied HCHO but not other carbonyl compounds PepP is a proline aminopeptidase that cleaves peptides of the general formula X-Pro-Y, yielding X + Pro-Y. HCHO is known to react spontaneously with cysteine to form the close proline analog thioproline (thiazolidine-4-carboxylate), which is incorporated into proteins and hence into proteolytic peptides. We therefore hypothesized that certain thioproline-containing peptides are toxic and that PepP cleaves these aberrant peptides. Supporting this hypothesis, PepP cleaved the model peptide Ala-thioproline-Ala as efficiently as Ala-Pro-Ala in vitro and in vivo, and deleting pepP increased sensitivity to supplied thioproline. Our data thus (i) provide biochem. genetic evidence that thioproline formation contributes substantially to HCHO toxicity and (ii) make PepP a candidate damage-control enzyme for engineered pathways having HCHO as an intermediate. In the experiment, the researchers used many compounds, for example, Thiazolidine-4-carboxylic acid (cas: 444-27-9Synthetic Route of C4H7NO2S).

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. 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.Synthetic Route of C4H7NO2S

Referemce:
Thiazolidine – Wikipedia,
Thiazolidine – ScienceDirect.com

Crystal structures of two triazola-dioxola-benzenacyclononaphanes was written by Viswanathan, Vijayan;Rao, Naga Siva;Raghunathan, Raghavachary;Velmurugan, Devadasan. And the article was included in Acta Crystallographica, Section E: Crystallographic Communications in 2015.Reference of 444-27-9 This article mentions the following:

In the title compounds, C₂₅H₂₉BrN₅O₇, (I) [systematic name: (Z)-1⁵-bromo-3²,3²-dimethyl-2¹-nitro-2²,2³,2⁵,2⁶,2⁷,2^7a,3^3a,3⁵,3⁶,3^6a-decahydro-2¹ H,6¹ H-4,9-dioxa-2(3,2)-pyrrolizina-6(4,1)-triazola-3(5,6)-furo[2,3-d][1,3]dioxola-1(1,2)-benzenacyclononaphane], and C₂₄H₂₉N₅O₇S, (II) [systematic name: (Z)-3²,3²-dimethyl-2⁷-nitro-2⁵,2⁶,2⁷,2^7a,3^3a,3⁵,3⁶,3^6a-octahydro-2¹ H,2³ H,6¹ H-4,9-dioxa-2(5,6)-pyrrolo[1,2-c]thiazola-6(4,1)-triazola-3(5,6)-furo[2,3-d][1,3]dioxola-1(1,2)-benzenacyclononaphane], the triazole rings adopt almost planar conformations. In (I), the fused pyrrolidine rings adopt envelope conformations with the C atoms opposite the fused N-C bond as the flap in each ring, and their mean planes are inclined to one another by 52.8 (3)°. In (II), the pyrrolidine and thiazole rings are both twisted on the fused N-C bond, and their mean planes are inclined to one another by 70.8 (2)°. In both (I) and (II), the furan ring adopts an envelope conformation with the adjacent C atom of the macrocycle as the flap. In the crystal of (I), mols. are linked via C-H···N and C-H···O hydrogen bonds, forming sheets parallel to (10-1), while in (II), mols. are linked via C-H···N and C-H···O hydrogen bonds, forming helical chains propagating along [010], which are linked via C-H···S hydrogen bonds, forming slabs parallel to (001). 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. Thiazolidine derivatives have been found to exhibit very prominent anti-inflammatory and anti-nociceptive activity. Open-chain compounds are obtained when thiazolidines are treated with tris(trimethylsilyl)silane in a reaction in which the thiazolidine derivatives act as a source of α-aminoalkyl radicals.Reference of 444-27-9

Referemce:
Thiazolidine – Wikipedia,
Thiazolidine – ScienceDirect.com

Design and synthesis of new substituted spirooxindoles as potential inhibitors of the MDM2-p53 interaction was written by Barakat, Assem;Islam, Mohammad Shahidul;Ghawas, Hussien Mansur;Al-Majid, Abdullah Mohammed;El-Senduny, Fardous F.;Badria, Farid A.;Elshaier, Yaseen A. M. M.;Ghabbour, Hazem A.. And the article was included in Bioorganic Chemistry in 2019.Formula: C4H7NO2S This article mentions the following:

The designed compounds, 4a-p, were synthesized using a simple and smooth method with an asym. 1,3-dipolar reaction as the key step. The chem. structures for all synthesized compounds were elucidated and confirmed by spectral anal. The mol. complexity and the absolute stereochem. of 4b and 4e designed analogs were determined by X-ray crystallog. anal. The anticancer activities of the synthesized compounds were tested against colon (HCT-116), prostate (PC-3), and hepatocellular (HepG-2) cancer cell lines. Mol. modeling revealed that the compound 4d binds through hydrophobic-hydrophobic interactions with the essential amino acids (LEU: 57, GLY: 58, ILE: 61, and HIS: 96) in the p53-binding cleft, as a standard p53-MDM2 inhibitor (6SJ). The mechanism underlying the anticancer activity of compound 4d was further evaluated, and the study showed that compound 4d inhibited colony formation, cell migration, arrested cancer cell growth at G2/M, and induced apoptosis through intrinsic and extrinsic pathways. Transactivation of p53 was confirmed by flow cytometry, where compound 4d increased the level of activated p53 and induced mRNA levels of cell cycle inhibitor, p21. In the experiment, the researchers used many compounds, for example, Thiazolidine-4-carboxylic acid (cas: 444-27-9Formula: C4H7NO2S).

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. 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.Formula: C4H7NO2S

Referemce:
Thiazolidine – Wikipedia,
Thiazolidine – ScienceDirect.com

Preparation of optically active 2-thiazolidinecarboxylic acid by asymmetric transformation was written by Shiraiwa, Tadashi;Katayama, Takashi;Ishikawa, Joji;Asai, Takeshi;Kurokawa, Hidemoto. And the article was included in Chemical & Pharmaceutical Bulletin in 1999.Application of 16310-13-7 This article mentions the following:

Cysteamine was condensed with glyoxylic acid monohydrate in a mixture of acetic acid and ethanol in the presence of (2R,3R)- or (2S,3S)-tartaric acid [(R)- or (S)-TA], as the resolving agent, to give the salt of (-)-2-thiazolidinecarboxylic acid [(-)-2-THC] with (R)-TA or the salt of (+)-2-THC with (S)-TA. Treatment of these salts with triethylamine in methanol afforded (-)- and (+)-2-THC, I and II resp. I and II were determined to be enantiopure forms by comparing their powder X-ray diffraction patterns with that of (RS)-2-THC. The absolute configurations of I and II were estimated based on molar rotations of (2R,4R)- and (2S,4R)-2,4-thiazolidinedicarboxylic acids, (R)-4-thiazolidinecarboxylic acid, and I and II. I was determined to have the (R)-configuration with II having the (S)-configuration. In the experiment, the researchers used many compounds, for example, Thiazolidine-2-carboxylic acid (cas: 16310-13-7Application of 16310-13-7).

Thiazolidine-2-carboxylic acid (cas: 16310-13-7) belongs to thiazolidine derivatives. Thiazolidine is an important scaffold and has a wide range of promising biological activities. Thiazolidine derivatives have reported anti-inflammatory and anti-nociceptive activity. 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 of 16310-13-7

Referemce:
Thiazolidine – Wikipedia,
Thiazolidine – ScienceDirect.com

Diversity-oriented one-pot multicomponent synthesis of chromanone-based 3,3′-pyrrolidinyl-spirooxindoles via a 1,3-dipolar cycloaddition reaction was written by Yue, Jing;Chen, Shuang;Zuo, Xiong;Liu, Xiong-Li;Xu, Sheng-Wen;Zhou, Ying. And the article was included in Tetrahedron Letters in 2019.Product Details of 444-27-9 This article mentions the following:

A new methodol. was developed for the highly efficient one-pot multicomponent synthesis of chromanone-based 3,3′-pyrrolidinyl-spirooxindoles via a 1,3-dipolar cycloaddition reaction of chromones with azomethine ylides (thermally generated in situ from isatins and proline or thioproline). Another valuable application of this method was for the less reactive chromone through a carboxylic acid-activation and then decarboxylation strategy, which enabled diversity-oriented synthesis of complex pirooxindoles bearing four contiguous stereocenters (one of which is a spiro quaternary stereocenter) with high efficiency and stereoselectivity (up to 90% yield and 20:1 d.r.). This protocol could provide libraries of stereochem. rich and multiple pharmecore collections, that will help in search for new drug-like mols. In the experiment, the researchers used many compounds, for example, Thiazolidine-4-carboxylic acid (cas: 444-27-9Product Details of 444-27-9).

Thiazolidine-4-carboxylic acid (cas: 444-27-9) belongs to thiazolidine derivatives. Thiazolidines undergo hydrolysis to aldehyde and amino thiol under acid or basic aqueous conditions. Thiazolidines are also used in peptide and protein modification, protein chemical synthesis, as activators to innate immunity and also act as immunostimulating agents.Product Details of 444-27-9

Referemce:
Thiazolidine – Wikipedia,
Thiazolidine – ScienceDirect.com

Thiazolidine-2-carboxylic acid, an adduct of cysteamine and glyoxylate, as a substrate for D-amino acid oxidase was written by Fitzpatrick, Paul F.;Massey, Vincent. And the article was included in Journal of Biological Chemistry in 1982.Recommanded Product: 16310-13-7 This article mentions the following:

A mixture of cysteamine and glyoxylate, proposed by G. A. Hamilton, et al. (1979) to form the physiol. substrate of hog kidney D-amino acid oxidase (I), was confirmed to act as a good substrate for the pure enzyme. As proposed by those workers, it was shown that the actual substrate is thiazolidine-2-carboxylic acid (II), formed from cysteamine and glyoxylate with a 2nd-order rate constant of 84 min^-1 M^-1 at 37°, pH 7.5. Steady state kinetic anal. revealed that II was a better substrate at pH 8.5 than at pH 7.5. At both pH values, the catalytic turnover number was similar to that obtained with D-proline. I was rapidly reduced by II to form a reduced enzyme-imino acid complex, as is typical with I substrates. The product of oxidation was shown by NMR to be Δ²-thiazoline-2-carboxylic acid. Racemic II was completely oxidized by I. The directly measured rate of isomerization of L–II to the D-isomer was compared to the rate of oxidation of the L-isomer by I. Their identity over the temperature range 2-30° established that the apparent activity with the L-amino acid can be explained quant. by the rapid, prior isomerization to D–II. In the experiment, the researchers used many compounds, for example, Thiazolidine-2-carboxylic acid (cas: 16310-13-7Recommanded Product: 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 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.Recommanded Product: 16310-13-7

Referemce:
Thiazolidine – Wikipedia,
Thiazolidine – ScienceDirect.com

A Convenient Synthesis of Fused Tetrahydroazocines from Acenaphthylene-1,2-dione, Proline, and Acetylenic Esters was written by Yavari, Issa;Baoosi, Leila;Halvagar, Mohammad Reza. And the article was included in Synlett in 2018.Related Products of 444-27-9 This article mentions the following:

A synthesis of dialkyl (12E,14E)-7-oxo-10,11-dihydro-7H,9H-azocino[2,1-a]benzo[de]isoquinoline-13,14-dicarboxylates through a 1,3-dipolar cycloaddition reaction of azomethine ylides, generated in situ from proline and acenaphthylene-1,2-dione, with dialkyl acetylenedicarboxylates is described. According to the X-ray diffraction data, the tetrahydroazocine ring has a rigid twist-boat form with approx. local C₂ symmetry. In the experiment, the researchers used many compounds, for example, Thiazolidine-4-carboxylic acid (cas: 444-27-9Related Products of 444-27-9).

Thiazolidine-4-carboxylic acid (cas: 444-27-9) 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 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.Related Products of 444-27-9

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

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

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