(R)-desmethyldesferrithiocin | 81744-98-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (R)-desmethyldesferrithiocin
• 英文别名: (R)-2-(3-hydroxypyridin-2-yl)-4,5-dihydrothiazole-4-carboxylic acid；(R)-Desmethyldesferrithiocin；(4R)-2-(3-hydroxypyridin-2-yl)-4,5-dihydro-1,3-thiazole-4-carboxylic acid
• CAS: 81744-98-1
• 化学式: C₉H₈N₂O₃S
• 分子量: 224.24
• InChiKey: TZIBMXCYUYRNRT-YFKPBYRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  108
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (R)-desmethyldesferrithiocin 在 盐酸 作用下， 反应 70.0h， 以65%的产率得到N-(3'-hydroxypyridin-2'-oyl)-L-cysteine
  参考文献：
  名称：

  Bergeron; Wollenweber; Wiegand, Journal of Medicinal Chemistry, 1994, vol. 37, # 18, p. 2889 - 2895

  摘要：

  DOI：
• 作为产物：
  描述：

  2-氰基-3-羟基吡啶 、 L-半胱氨酸 以85%的产率得到
  参考文献：
  名称：

  BERGERON, RAYMOND J.;WIEGAND, JAN;DIONIS, JOHN B.;EGLI-KARMAKKA, MAJIA;FR+, J. MED. CHEM., 34,(1991) N, C. 2072-2078

  摘要：

  DOI：

文献信息

• Evaluation of desferrithiocin and its synthetic analogs as orally effective iron chelators
  作者：Raymond J. Bergeron、Jan Wiegand、John B. Dionis、Majia Egli-Karmakka、Joerg Frei、Alica Huxley-Tencer、Heinrich H. Peter

  DOI：10.1021/jm00111a023

  日期：1991.7

  Desferrithiocin, a novel microbial siderophore isolated from cultures of Streptomyces antibioticus DSM 1865, and a number of its derivatives and analogues are evaluated for their ability to promote iron clearance. The compounds have been designed with the objective of identifying the structural features of desferrithiocin which render this ligand an orally effective iron chelator. The desferrithiocin aromatic hydroxyl and the thiazoline ring carboxyl group are shown to be central to desferrithiocin's activity. The ligand's methyl and the aromatic nitrogen play little role in the compound's efficacy. The animal model chosen for this study, the bile duct cannulated rat, provides information regarding both the chelator-induced total iron output and the kinetics of both biliary and urinary iron excretion.
• COMPOSITIONS AND METHODS FOR PREVENTING AND TREATING MUCOSITIS AND WEIGHT LOSS
  申请人：Prendergast Patrick T.

  公开号：US20100092547A1

  公开（公告）日：2010-04-15

  A method for prophylaxis and/or treatment of mucositis comprising the steps of providing a therapeutically effective amount of a composition comprising either (1) at least one compound selected from the group consisting of 5-[2-pyrazinyl]-4-methyl-1,2-3-thione or an analogue, derivative, metabolite, prodrug, solvate or a pharmaceutically acceptable salt thereof; or (2) a cytokinin compound; and administering the composition to a subject in need of such treatment. Also provided are pharmaceutical compositions comprising 5-[2-pyrazinyl]-4-methyl-1,2-3-thione and/or a cytokinin compound and use of these compositions in the preparation of a medicament for the treatment and/or prophylaxis of mucositis. The cytokinin compound may be selected from, but is not limited to N 6 -isopentenyl adenosine and N 6 -benzyl adenosine. The compositions may further comprise a chemotherapeutic agent, such as cisplatin. Further provided are methods and compositions for reducing and/or preventing weight loss in subjects undergoing cancer treatment.
• Compositions and Methods for Preventing and Treating Mucositis and Weight Loss
  申请人：Cascade Estate Ltd.

  公开号：US20130259930A1

  公开（公告）日：2013-10-03

  Pharmaceutical compositions comprising 5-[2-pyrazinyl]-4-methyl-1,2-3-thione or an analogue, derivative, metabolite, prodrug, solvate or a pharmaceutically acceptable salt thereof; and a pharmaceutical carrier, which promotes association with the outer wall of a subject's digestive tract are described as well as their uses in treating and preventing mucositis and cachexia.
• [EN] PHENOL DERIVATIVES AND METHODS OF USE THEREOF<br/>[FR] DÉRIVÉS DE PHÉNOL ET LEURS PROCÉDÉS D'UTILISATION
  申请人：CRYSTALGENOMICS INC

  公开号：WO2010018458A2

  公开（公告）日：2010-02-18

  Disclosed herein are hydroxyaryl or hydroxyheteroaryl derivative compounds, or a pharmaceutically acceptable salt, ester, amide, or prodrug thereof, pharmaceutical compositions comprising the same, and methods of modulating the level or activity of HIF in a subject, inhibiting hydroxylation of HIFα in a subject, modulating expression of HIF-regulated genes in a subject, treating an HIF -related disorder in a subject, increasing levels of endogenous EPO in a subject, or treating a disorder in a subject, using the disclosed compounds.
• [EN] USE OF METAL CHELATORS IN MANAGING INFECTIOUS DISEASES<br/>[FR] UTILISATION DE CHÉLATEURS DE MÉTAUX DANS LA GESTION DE MALADIES INFECTIEUSES
  申请人：UNIV FLORIDA

  公开号：WO2016154547A1

  公开（公告）日：2016-09-29

  The present invention provides methods using a compound capable of chelating a metal (e.g., iron) for treating and/or preventing infectious diseases. In particular, the metal chelators are desferrithiocin analogs, desazadesfemthiocin analogs, and HBED analogs of Formula (I-A)-(III-A). The invention further provides methods useful in inhibiting biofilm formation. The provided methods also include combination therapies comprising a metal chelator with another therapeutic agent (e.g., antibiotic). The infectious diseases and/or biofilm formation may occur in a subject diagnosed with cystic fibrosis.