thiazolidine

チアゾリジン

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/12/25 23:37:49」(JST)

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Thiazolidine

Names
IUPAC name Thiazolidine
Identifiers
CAS Number	504-78-9 Y
Jmol interactive 3D	Image
PubChem	10444
SMILES C1CSCN1
Properties
Chemical formula	C3H7NS
Molar mass	89.16 g/mol
Density	1.131 g/cm3
Boiling point	72 to 75 °C (162 to 167 °F; 345 to 348 K) at 25 torr
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is YN ?)
Infobox references

Thiazolidines are a class of heterocyclic organic compounds with a 5-membered saturated ring with a thioether group and an amine group in the 1 and 3 positions, respectively. It is a sulfur analogue of oxazolidine. The drug pioglitazone contains a thiazolidine ring. It is a drug usually indicated in cases of type II diabetes for decreasing blood sugar. It also decreases triglycerides and C-reactive protein levels. It lowers blood pressure and increases levels of HDL. Another drug which contains a thiazolidine ring is the antibiotic drug penicillin.

Thiazolidines may be synthesized by a condensation reaction between a thiol and an aldehyde or ketone. The reaction is reversible. Therefore, many thiazolidines are labile towards hydrolysis in aqueous solution. Hydrolysis of the thiazolidine generates the thiol and aldehyde or ketone from which it was synthesized.

Thiazolidine with 2 ketones (at the 2 and 4 positions) provides the functional group of the thiazolidinediones.

References

English Journal

• An asymmetric alkynylation/hydrothiolation cascade: an enantioselective synthesis of thiazolidine-2-imines from imines, acetylenes and isothiocyanates.

• Ranjan A1, Mandal A, Yerande SG, Dethe DH.
• Chemical communications (Cambridge, England).Chem Commun (Camb).2015 Sep 28;51(75):14215-8. doi: 10.1039/c5cc05549k. Epub 2015 Aug 10.
• A multicomponent reaction between imines, terminal alkynes, and isothiocyanates in the presence of a catalytic chiral copper-pybox complex proceeds enantioselectively to give enantiopure thiazolidine-2-imines (60-99% ee) via a highly regioselective intramolecular 5-exo-dig hydrothiolation reaction.
• PMID 26255639

• Synthesis and antiviral activity of some new bis-1,3-thiazole derivatives.

• Dawood KM1, Eldebss TM2, El-Zahabi HS3, Yousef MH2.
• European journal of medicinal chemistry.Eur J Med Chem.2015 Sep 18;102:266-76. doi: 10.1016/j.ejmech.2015.08.005. Epub 2015 Aug 5.
• Treatment of 3-phenyl-1,3-thiazolidin-4-one derivative 1 with phenylisothiocyanate in DMF, in the presence of potassium hydroxide, at room temperature gave the non-isolable potassium salt 2. The in-situ reaction of 2 with differently substituted N-aryl hydrazonoyl chlorides 3, 7a-d and 14a-d afforde
• PMID 26291036

• Combination of DPP-4 inhibitor and PPARγ agonist exerts protective effects on pancreatic β-cells in diabetic db/db mice through the augmentation of IRS-2 expression.

• Hirukawa H1, Kaneto H2, Shimoda M2, Kimura T2, Okauchi S2, Obata A2, Kohara K2, Hamamoto S2, Tawaramoto K2, Hashiramoto M3, Kaku K4.
• Molecular and cellular endocrinology.Mol Cell Endocrinol.2015 Sep 15;413:49-60. doi: 10.1016/j.mce.2015.06.010. Epub 2015 Jun 25.
• We investigated the effects of long- and short-term treatment with pioglitazone (Pio) and/or alogliptin (Alo) on β-cells in diabetic db/db mice. Six-week-old male db/db mice received Pio (25 mg/kg, oral) and/or Alo (30 mg/kg, oral) for 4 weeks and for 2 days. Blood glucose levels were decreased a
• PMID 26116826

Japanese Journal

• SYNTHESIS AND ANTICANCER ACTIVITIES OF THIAZOLES, 1,3-THIAZINES, AND THIAZOLIDINE USING CHITOSAN-GRAFTED-POLY (VINYLPYRIDINE) AS BASIC CATALYST

• Gomha Sobhi M.,Riyadh Sayed M.,Mahmmoud Elmahdi A. [他]
• Heterocycles : an international journal for reviews and communications in heterocyclic chemistry 91(6), 1227-1243, 2015-06-01
• NAID 40020504790

• チアゾリジン薬 (特集 糖尿病治療薬update : 適正な血糖管理を目指して) -- (糖尿病治療薬の薬効と適応基準)

• 小林 正稔,植木 浩二郎
• 日本臨床 73(3), 402-408, 2015-03
• NAID 40020367026

• Synthesis and Evaluation of 5-(3-(Pyrazin-2-yl)benzylidene)thiazolidine-2,4-dione Derivatives as Pan-Pim Kinases Inhibitors

• Lee Jinho,Park Jongseong,Hong Victor Sukbong
• Chemical and pharmaceutical bulletin 62(9), 906-914, 2014-09
• NAID 40020173344

Related Links

• チアゾリジン誘導体 - 脂質と血栓の医学

チアゾリジン（thiazolidine ）誘導体は、脂肪細胞の核内受容体型転写因子PPARγに結合し、試験管内（in vitro）で、（グルコールの消費を促進させ、）脂肪細胞の分化を促進する（肝臓や筋肉で中性脂肪の蓄積が促進する ）。 注1 ...

• Thiazolidine 504-78-9 | 東京化成工業株式会社

[Thiazolidine] [504-78-9] | 価格や在庫、物性値などの詳細情報ページです。 ... ・川口の在庫は即日，つくばの在庫は2〜3日以内の出荷となります。・詳細につきましては，お手数ですが営業部までお問い合わせください。

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