N-acetyl-N'-(tert-butoxycarbonyl)-N,N'-dihydroxy-1,5-pentadiamine | 155880-08-3

• 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: N-acetyl-N'-(tert-butoxycarbonyl)-N,N'-dihydroxy-1,5-pentadiamine
• 英文别名: tert-butyl N-[5-[acetyl(hydroxy)amino]pentyl]-N-hydroxycarbamate
• CAS: 155880-08-3
• 化学式: C₁₂H₂₄N₂O₅
• 分子量: 276.333
• InChiKey: OTVKCSLMNXOTKB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  90.3
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-acetyl-N'-(tert-butoxycarbonyl)-N,N'-dihydroxy-1,5-pentadiamine 、 三氟乙酸 以 二氯甲烷 为溶剂， 以100%的产率得到N-acetyl-N,N'-dihydroxy-1,5-pentanediamine trifluoroacetate
  参考文献：
  名称：

  The Desferrithiocin Pharmacophore

  摘要：

  The (S)-desferrithiocin (DFT) skeleton is shown to be a useful pharmacophore on which to design orally effective iron chelators. While the study clearly indicates that formal reduction of the desazadesmethyldesferrithiocin thiazoline to a thiazolidine (6), expansion of the desmethyldesferrithiocin thiazoline to a thiazine (7), or substitution of the thiazoline sulfur of desazadesmethyldesferrithiocin by an oxygen (8 and 9) lead to a substantial loss of activity, conversion of (S)-desmethyldesferrithiocin (1) to an N-methylhydroxamate (4) or to the hexacoordinate dihydroxamate ligand (5) results in active compounds. This investigation thus demonstrates which structural components of the siderophore are required for iron clearance after oral administration and suggests the use of the desferrithiocin platform as a vector for other chelators.

  DOI：

  10.1021/jm00036a005
• 作为产物：
  描述：

  N-(苄氧基)氨基甲酸叔丁酯 在 palladium on activated charcoal 氢气 、 sodium hydride 作用下， 以 甲醇 为溶剂， 80.0 ℃ 、101.33 kPa 条件下， 反应 3.67h， 生成 N-acetyl-N'-(tert-butoxycarbonyl)-N,N'-dihydroxy-1,5-pentadiamine
  参考文献：
  名称：

  The Desferrithiocin Pharmacophore

  摘要：

  The (S)-desferrithiocin (DFT) skeleton is shown to be a useful pharmacophore on which to design orally effective iron chelators. While the study clearly indicates that formal reduction of the desazadesmethyldesferrithiocin thiazoline to a thiazolidine (6), expansion of the desmethyldesferrithiocin thiazoline to a thiazine (7), or substitution of the thiazoline sulfur of desazadesmethyldesferrithiocin by an oxygen (8 and 9) lead to a substantial loss of activity, conversion of (S)-desmethyldesferrithiocin (1) to an N-methylhydroxamate (4) or to the hexacoordinate dihydroxamate ligand (5) results in active compounds. This investigation thus demonstrates which structural components of the siderophore are required for iron clearance after oral administration and suggests the use of the desferrithiocin platform as a vector for other chelators.

  DOI：

  10.1021/jm00036a005

文献信息

• [EN] 2-(PYRID-2'-YL)-2-THIAZOLINE-4(S)-CARBOXYLIC ACID DERIVATIVES<br/>[FR] DERIVES D'ACIDE 2-(PYRID-2'-YL)-2-THIAZOLINE-4(S)-CARBOXYLIQUE
  申请人：UNIVERSITY OF FLORIDA RESEARCH FOUNDATION INC.

  公开号：WO1994011367A1

  公开（公告）日：1994-05-26

  (EN) 2-(Pyrid-2'-yl)-2-thiazoline-4-carboxylic acid derivatives of formula (I) in which R1 represents hydrogen, halogen, hydroxy, C1-C4 alkoxy or C1-C4 alkyl; R2 represents hydroxy or resterified hydroxy; and R3 represents etherified hydroxy or a group of the partial formula -N(R4, R5) in which R4 and R5 independently from each other represent hydrogen or C1-C4 alkyl or in which R4 represents hydroxy or esterified hydroxy and R5 represents hydrogen, C1-C4 alkyl or a group -X-R6 in which X is C2-C12 alkylen or oxaalkylen having 4-12 chain members and R6 represents C1-C2 alkyl or a hydroxylamino group -N(OH)-R7 in which R7 represents C1-C4 alkanoyl; and salts thereof form chelate-type metal complexes with trivalent metal ions, especially iron (III), and can be used, for example, for the treatment of pathological conditions in warm-blooded animals that are associated with an excess of trivalent metal ions in the body. Valuable starting material embraces alkali and alkaline earth salts of 2-(3'hydroxypyrid-2'-yl)-2-thiazoline-4(S)-carboxylic acid.(FR) Dérivés d'acide 2-(pyrid-2'-yl)-2-thiazoline-4(S)-carboxylique de la formule (I) dans laquelle R1 représente hydrogène, un halogène, un hydroxy, un alcoxy C1-C4 ou un alkyle C1-C4; R2 représente un hydroxy ou un hydroxy estérifié; et R3 représente un hydroxy éthérifié ou un groupe représenté par la formule partielle -N(R4, R5) dans laquelle R4 et R5 représentent, indépendamment l'un de l'autre, hydrogène ou un alkyle C1-C4 ou bien dans laquelle R4 représente un hydroxy ou un hydroxy estérifié et R5 représente hydrogène, un alkyle C1-C4 ou un groupe -X-R6 dans lequel X est un alkylène C2-C12 ou un oxaalkylène comptant de 4 à 12 éléments de chaîne et R6 représente un alkyle C1-C2 ou un groupe hydroxylamino -N(OH)-R7 dans lequel R7 représente un alcanoyle C1-C4. Ces composés et leurs sels forment des complexes métalliques du type chélate renfermant des ions métalliques trivalents, notamment des ions ferriques, et peuvent être utilisés, par exemple, pour le traitement, chez les êtres à sang chaud, des états pathologiques liés à un excès d'ions métalliques trivalents dans l'organisme. Les sels alcalins et alcalino-terreuux d'acide 2-(3'hydroxypyrid-2'-yl)-2-thiazoline-4(S)-carboxylique constituent des matières de départ avantageuses.

  化合物的化学式为(I)，其中R1代表氢、卤素、羟基、C1-C4烷氧基或C1-C4烷基；R2代表羟基或酯化羟基；R3代表醚化羟基或部分式-N(R4，R5)的基团，其中R4和R5独立地表示氢或C1-C4烷基，或者R4表示羟基或酯化羟基，而R5表示氢、C1-C4烷基或-X-R6的基团，其中X为C2-C12烷基或4-12链成员的氧杂烷基，而R6表示C1-C2烷基或羟胺基-N(OH)-R7，其中R7表示C1-C4烷酰基；它们的盐与三价金属离子，特别是铁（III）形成螯合型金属络合物，可用于治疗与体内三价金属离子过多有关的温血动物的病理状况。有价值的起始材料包括2-(3'羟基吡啶-2'-基)-2-噻唑啉-4(S)-羧酸的碱金属和碱土金属盐。
• The Desferrithiocin Pharmacophore
  作者：Raymond J. Bergeron、Charles Z. Liu、James S. McManis、Michael X. B. Xia、Samuel E. Algee、Jan Wiegand

  DOI：10.1021/jm00036a005

  日期：1994.5

  The (S)-desferrithiocin (DFT) skeleton is shown to be a useful pharmacophore on which to design orally effective iron chelators. While the study clearly indicates that formal reduction of the desazadesmethyldesferrithiocin thiazoline to a thiazolidine (6), expansion of the desmethyldesferrithiocin thiazoline to a thiazine (7), or substitution of the thiazoline sulfur of desazadesmethyldesferrithiocin by an oxygen (8 and 9) lead to a substantial loss of activity, conversion of (S)-desmethyldesferrithiocin (1) to an N-methylhydroxamate (4) or to the hexacoordinate dihydroxamate ligand (5) results in active compounds. This investigation thus demonstrates which structural components of the siderophore are required for iron clearance after oral administration and suggests the use of the desferrithiocin platform as a vector for other chelators.