- Discovery of cysteine and its derivatives as novel antiviral and antifungal agents
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Based on the structure of the natural product cysteine, a series of thiazolidine-4-carboxylic acids were designed and synthesized. All target compounds bearing thiazolidine-4-carboxylic acid were characterized by1 H-NMR,13 C-NMR, and
- Lu, Aidang,Shi, Li,Wang, Tienan,Wang, Ziwen,Yang, Shan,Zhou, Yanan
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- GLUCOSE-SENSITIVE PEPTIDE HORMONES
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The present invention relates to a conjugate of the formula P-L-I, wherein P is a peptide hormone effecting the metabolism of carbohydrates in vivo, L is a hydrolysable linker molecule consisting of Lp and Lj, and I is a molecule capable of inhibiting the effect of the peptide hormone P on the metabolism of carbohydrates in vivo. Under in vivo conditions, the conjugate is the major compound. When the concentration of glucose increases in v/vo,the concentration of the peptide hormone effecting the metabolism of carbohydrates in vivo also increases.
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Page/Page column 26
(2020/01/11)
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- Purple acid phosphatase inhibitors as leads for osteoporosis chemotherapeutics
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Purple acid phosphatases (PAPs) are metalloenzymes that catalyse the hydrolysis of phosphate esters under acidic conditions. Their active site contains a Fe(III)Fe(II) metal centre in mammals and a Fe(III)Zn(II) or Fe(III)Mn(II) metal centre in plants. In humans, elevated PAP levels in serum strongly correlate with the progression of osteoporosis and metabolic bone malignancies, which make PAP a target suitable for the development of chemotherapeutics to combat bone ailments. Due to difficulties in obtaining the human enzyme, the corresponding enzymes from red kidney bean and pig have been used previously to develop specific PAP inhibitors. Here, existing lead compounds were further elaborated to create a series of inhibitors with Ki values as low as ~30 μM. The inhibition constants of these compounds were of comparable magnitude for pig and red kidney bean PAPs, indicating that relevant binding interactions are conserved. The crystal structure of red kidney bean PAP in complex with the most potent inhibitor in this series, compound 4f, was solved to 2.40 ? resolution. This inhibitor coordinates directly to the binuclear metal centre in the active site as expected based on its competitive mode of inhibition. Docking simulations predict that this compound binds to human PAP in a similar mode. This study presents the first example of a PAP structure in complex with an inhibitor that is of relevance to the development of anti-osteoporotic chemotherapeutics.
- Hussein, Waleed M.,Feder, Daniel,Schenk, Gerhard,Guddat, Luke W.,McGeary, Ross P.
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p. 462 - 479
(2018/08/21)
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- 3-Propionyl-thiazolidine-4-carboxylic acid ethyl esters: A family of antiproliferative thiazolidines
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Cancer results from unregulated cell growth. Reactivating the process of the programmed cell death, i.e. apoptosis, is a classical anticancer therapeutic strategy. The apoptosis-inducing property of the (2RS,4R)-2-phenyl-3-propionyl-thiazolidine-4-carboxylic acid ethyl ester (ALC 67) molecule has recently been discovered. We analyzed in this study the impact of the phenyl moiety of this molecule on its biological activity by synthesizing and evaluating analogues where this substituent was replaced by a series of aromatic and aliphatic groups. The results demonstrated that the molecule's antiproliferative property resisted such modifications. Thus, in addition to developing a family of thiazolidine compounds with promising anticancer properties; our investigation revealed that the second position of the thiazolidine ring can be used either to tune the physicochemical properties of ALC67 or to introduce a fluorescent tag to the structure in order to track it in cells and determine its exact molecular mechanism of action.
- ?nen-Bayram, F. Esra,Buran, Kerem,Durmaz, Irem,Berk, Barkin,Cetin-Atalay, Rengul
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supporting information
p. 90 - 93
(2015/02/05)
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- Synthesis, characterization and antibacterial activities of N-tert-butoxycarbonyl-thiazolidine carboxylic acid
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A possible mechanism of dynamic kinetic resolution by the formation of N-tert-butoxycarbonyl-thiazolidine carboxylic acid was proposed and validated by a quantitative density functional theoretical calculation according to Curtin-Hammett principle. Such a
- Song, Zhong-Cheng,Ma, Gao-Yuan,Zhu, Hai-Liang
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p. 24824 - 24833
(2015/03/30)
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- NOVEL COMPOUND HAVING SKIN-WHITENING, ANTI-OXIDIZING AND PPAR ACTIVITIES AND MEDICAL USE THEREFOR
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Provided are a novel compound having skin-whitening, anti-oxidizing and PPAR activities and a medical use thereof, and the compound has skin-whitening activities for the suppression of tyrosinase, and accordingly, is useful for use in skin-whitening pharmaceutical composition or cosmetic products; has anti-oxidant activities, and accordingly, is useful for the prevention and treatment of skin-aging; and has PPAR activities, and in particular, PPARα and PPARγ activities, and accordingly, is useful for use in pharmaceutical compositions or health foods which are effective for the prevention and treatment of obesity, metabolic disease, or cardiovascular disease.
- -
-
Paragraph 0135-0137; 0145
(2014/02/16)
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- Substituent-dependent reactivity in aldehyde transformations: 4-(phenylethynyl)benzaldehydes versus simple benzaldehydes
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Effects of substituents on transformations of 4-(phenylethynyl) benzaldehydes and related benzaldehydes were analyzed in aldol and thiazolidine formation reactions. The aldol reaction of 4-cyanobenzaldehyde was 54-fold faster than that of 4-methoxybenzald
- Katsuyama, Isamu,Chouthaiwale, Pandurang V.,Cui, Hai-Lei,Ito, Yuji,Sando, Ayumi,Tokiwa, Hiroaki,Tanaka, Fujie
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supporting information
p. 4098 - 4104
(2013/07/31)
-
- Design, synthesis and biological evaluation of 2-(substituted phenyl)thiazolidine-4-carboxylic acid derivatives as novel tyrosinase inhibitors
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Herein we describe the design, synthesis and biological activities of 2-(substituted phenyl)thiazolidine-4-carboxylic acid derivatives as novel tyrosinase inhibitors. The target compounds 2a-2j were designed and synthesized from the structural characteristics of N-phenylthiourea, tyrosinase inhibitor and tyrosine, and l-DOPA, the natural substrates of tyrosinase. Among them, (2R/S,4R)-2-(2,4-dimethoxyphenyl)thiazolidine-4-carboxylic acid (2g) caused the greatest inhibition 66.47% at 20 μM of l-DOPA oxidase activity of mushroom tyrosinase. Kinetic analysis of tyrosinase inhibition revealed that 2g is a competitive inhibitor. We predicted the tertiary structure of tyrosinase, and simulated the docking of mushroom tyrosinase with 2g. These results suggest that the binding affinity of 2g with tyrosinase is high. Also, 2g effectively inhibited tyrosinase activity and reduced melanin levels in B16 cells treated with α-MSH. These data strongly suggest that 2g can suppress the production of melanin via the inhibition of tyrosinase activity.
- Ha, Young Mi,Park, Yun Jung,Lee, Ji Yeon,Park, Daeui,Choi, Yeon Ja,Lee, Eun Kyeong,Kim, Ji Min,Kim, Jin-Ah,Park, Ji Young,Lee, Hye Jin,Moon, Hyung Ryong,Chung, Hae Young
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experimental part
p. 533 - 540
(2012/05/20)
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- BIOMOLECULAR LABELLING USING MULTIFUNCTIONAL BIOTIN ANALOGUES
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Novel biotin analogues, such as 2-Azidobiotin, comprising the ureido ring of natural biotin with the thiophene ring, optionally modified, and a modified sidechain having a functional end group, preferably selected from the group consisting of a carboxylic
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Page/Page column 49
(2010/10/03)
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- Synthesis, in vitro structure-activity relationship, and in vivo studies of 2-arylthiazolidine-4-carboxylic acid amides as anticancer agents
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A series of (2RS,4R)-2-arylthiazolidine-4-carboxylic acid amide (ATCAA) was synthesized. Antiproliferative activity against melanoma and prostate cancer cells compared with control cells (fibroblast and RH7777, respectively) was evaluated. Compound 3id sh
- Lu, Yan,Wang, Zhao,Li, Chien-Ming,Chen, Jianjun,Dalton, James T.,Li, Wei,Miller, Duane D.
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experimental part
p. 477 - 495
(2010/04/29)
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- Synthesis, structure and structure-activity relationship analysis of 3-tert-butoxycarbonyl-2-arylthiazolidine-4-carboxylic acid derivatives as potential antibacterial agents
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Nine 2-arylthiazolidine-4-carboxylic acid derivatives and nine 3-tert-butoxycarbonyl-2-arylthiazolidine-4-carboxylic acid derivatives were synthesized to screen for their antibacterial activities. Compounds 5, 14-18 were first reported. Their chemical str
- Song, Zhong-Cheng,Ma, Gao-Yuan,Lv, Peng-Cheng,Li, Huan-Qiu,Xiao, Zhu-Ping,Zhu, Hai-Liang
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experimental part
p. 3903 - 3908
(2009/12/04)
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- HETEROCYCLIC CARBOXYLIC ACID DERIVATIVES AND PHARMACEUTICAL COMPOSITION FOR INHIBITING LIPID ACCUMULATION CONTAINING SAME
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The present invention relates to a novel heterocyclic carboxylic acid derivative, or a pharmaceutically acceptable salt thereof, and a pharmaceutical composition comprising the same as an active ingredient for inhibiting the accumulation of lipids in the body.
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Page/Page column 64-65
(2008/12/04)
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- AMIDO ANTI-VIRAL COMPOUNDS
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Disclosed are compounds, stereoisomers, tautomers, pharmaceutically acceptable salts, or prodrugs thereof of having Formula (I), their preparation, use, and compositions thereof for treating an infection mediated at least in part by a virus in the Flaviviridae family of viruses, wherein A, R3, X, V, W, T, Z, R, Y1, and p are as defined herein.
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Page/Page column 90
(2008/12/05)
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- PROCESS FOR THE PREPARATION OF 3,4-DISUBSTITUTED-THIAZOLIDIN-2-ONES
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The present invention is directed to practical high-yielding synthetic processes for preparing 3,4-disubstituted-thiazolidin-2-ones, which do not compromise the absolute stereochemical integrity of the compounds. The present invention is also directed to
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Page/Page column 12; 14
(2010/11/28)
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- Cytoskeletal active compounds, compositions and use
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The present invention is directed to synthetic cytoskeletal active compounds that are related to natural Latrunculin A or Latrunculin B. The present invention is also directed to pharmaceutical compositions comprising such compounds and a pharmaceutically
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Page/Page column 19
(2010/11/23)
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- Discovery of 2-arylthiazolidine-4-carboxylic acid amides as a new class of cytotoxic agents for prostate cancer
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To improve the selectivity and antiproliferative activity of previously reported serine amide phosphates (SAPs), we designed a new series of 4-thiazolidinone amides, in which the 4-thiazolidinone moiety was introduced as a phosphate mimic. However, these 4-thiazolidinone derivatives demonstrated less cytotoxicity in prostate cancer cells despite improved selectivity over RH7777 cells. To further optimize the thiazolidinone analogues in terms of cytotoxicity and selectivity, we made closely related structural modifications, which led us to the discovery of a new class of 2-arylthiazolidine-4-carboxylic acid amides. These compounds were potent cytotoxic agents with IC50 values in the low micromolar concentration range and demonstrated enhanced selectivity in receptor-negative cells compared to SAPs and 4-thiazolidinone amides.
- Gududuru, Veeresa,Hurh, Eunju,Dalton, James T.,Miller, Duane D.
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p. 2584 - 2588
(2007/10/03)
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- New C2-symmetric chiral disulfide ligands derived from (R)-cysteine
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Several sulfur-containing optically active C2-symmetrical ligands have been synthesized from (R)-cysteine and applied successfully as chiral catalysts in the asymmetric addition of diethylzinc to aldehydes. The resulting secondary alcohols could be obtained in good yields and excellent enantiomeric excess.
- Braga, Antonio L,Appelt, Helmoz R,Schneider, Paulo H,Rodrigues, Oscar E.D,Silveira, Claudio C,Wessjohann, Ludger A
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p. 3291 - 3295
(2007/10/03)
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- Azafulvenium methides: New extended dipolar systems
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The transient 1-azafulvenium methides 24, 26 and 28 generated by thermal extrusion of sulfur dioxide from pyrrolo[1,2-c][1,3]thiazole 2,2-dioxide 20 (R = Me), 22 and 23 undergo sigmatropic [1,8]H shifts and the 1-acyl derivatives 30 electrocyclise to give novel pyrrolo[1,2-c][1,3]oxazines 32. The analogous 1,2-diazafulvenium methide 36 has been intercepted in [8π + 2π] cycloadditions with electron-rich silylated acetylenes to give adducts 37-40. This behaviour is partially explained by Frontier MO theory.
- Sutcliffe, Oliver B.,Storr, Richard C.,Gilchrist, Thomas L.,Rafferty, Paul
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p. 1795 - 1806
(2007/10/03)
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- Enhancing the proline effect: Pseudo-prolines for tailoring Cis/ trans isomerization
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Cis-trans isomerization of proline-like oxazolidines and thiazolidines, denoted pseudo-prolines, is investigated spectrophotometrically with a chymotrypsin coupled assay and by 1H NMR. A series of peptides carrying substituents of varying stere
- Keller, Michael,Sager, Cédric,Dumy, Pascal,Schutkowski, Mike,Fischer, Gunter S.,Mutter, Manfred
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p. 2714 - 2720
(2007/10/03)
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- Two new procedures for the introduction of benzyl-type protecting groups for thiols
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Two new methods for the benzylation of thiols are described: a) direct-S- alkylation with para-substituted benzylic cations; and b) reductive S- alkylations of 2-aminothiols. Both methods provide efficient routes for the introduction of benzyl-type protecting groups in high yields.
- Richter, Lutz S.,Marsters Jr., James C.,Gadek, Thomas R.
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p. 1631 - 1634
(2007/10/02)
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- Synthesis and Chiroptical Properties of N-Acetyl-2-aryl-4-thiazolidinecarboxylic Acids
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(4R)-2-Aryl-4-thiazolidinecarboxylic acids 3, derived from aromatic aldehydes 1 and L-cysteine (2), could be diastereoselectively converted into (2R,4R)- or (2S,4R)-N-acetyl-2-aryl-4-thiazolidinecarboxylic acids (4 and 5, resp.).The diastereomers can be d
- Gyoergydeak, Zoltan,Kajtar-Peredy, Maria,Kajtar, Judit,Kajtar, Marton
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p. 927 - 934
(2007/10/02)
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