3-phthalimido-propionamide | 4443-33-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 3-phthalimido-propionamide
• 英文别名: N-(phthalimidomethyl)acetamide；3-(1,3-dioxo-1,3-dihydroisoindol-2-yl)propionamide；β-Phthalimido-propionsaeure-amid；Phthalyl-β-alaninamid；N,N-phthaloyl-β-alanine amide；N,N-Phthaloyl-β-alanin-amid；3-(1,3-Dioxoisoindol-2-yl)propanamide
• CAS: 4443-33-8
• 化学式: C₁₁H₁₀N₂O₃
• mdl: MFCD00447752
• 分子量: 218.212
• InChiKey: DVPXSKBBAJCTJS-UHFFFAOYSA-N

物化性质

• 熔点：
  203-204 °C
• 沸点：
  467.5±28.0 °C(Predicted)
• 密度：
  1.385±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.181
• 拓扑面积：
  80.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-phthalimido-propionamide 在 氯化亚砜 、 水 、 三乙胺 作用下， 以 丙酮 、 甲苯 、 乙腈 为溶剂， 反应 20.0h， 生成 2-(2-(1,3-dioxoisoindolin-2-yl)ethyl)-5-(4-methylpiperazin-1-yl)oxazole-4-carbonitrile
  参考文献：
  名称：

  Synthesis and some properties of 5-alkylamino-2-(phthalimidoalkyl)-1,3-oxazole-4-carbonitriles

  摘要：

  5-Alkylamino-1,3-oxazole-4-carbonitriles containing a 2-phthalimidoethyl or 3-phthalimidopropyl substituent at position 2 of the oxazole ring were synthesized. In the reaction of 5-(morpholin-4-yl)-2-(2-phthalimidoethy) l-1,3-oxazole-4-carbonitrile with hydrazine hydrate, 2-(2-aminoethyl)-5-(morpholin-4-yl)-1,3-oxazole-4-carbonitrile is formed. In the case of the 3-phthalimidopropyl analog, the recyclization product 3-amino-2-(morpholin-4-ylcarbonyl)-6,7-dihydro-5H-pyrrolo[1,2-a] imidazole is formed.

  DOI：

  10.1007/s10593-011-0869-y
• 作为产物：
  描述：

  N-(2-氰基乙基)-邻苯二甲酰亚胺 在 硫酸 作用下， 生成 3-phthalimido-propionamide
  参考文献：
  名称：

  The Reaction of N-Hydroxymethyl Phthalimide with Nitriles

  摘要：

  DOI：

  10.1021/ja01194a024

文献信息

• Synthesis and anticonvulsant activity ofN,N-phthaloyl derivatives of central nervous system inhibitory amino acids
  作者：Cyril O. Usifoh、Didier M. Lambert、Johan Wouters、Gerhard K. E. Scriba

  DOI：10.1002/1521-4184(200110)334:10<323::aid-ardp323>3.0.co;2-o

  日期：2001.10

  of the amino acid chain of N,N‐phthaloylamino acid amides as analogues of the former anticonvulsant taltrimide on the seizureantagonizing activity glycine, β‐alanine and γ‐aminobutyric acid (GABA) derivatives were synthesized. The corresponding taurine derivatives were also included. Generally, the glycine‐derived amides showed a higher activity than the β‐alanine and GABA derivatives in the maximal

  为了研究作为前抗惊厥药他曲酰亚胺类似物的 N,N-邻苯二甲酰氨基酸酰胺的氨基酸链长度对癫痫拮抗活性甘氨酸的影响，合成了 β-丙氨酸和 γ-氨基丁酸 (GABA) 衍生物。还包括相应的牛磺酸衍生物。一般来说，在小鼠腹膜内给药的最大电休克癫痫 (MES) 试验中，甘氨酸衍生的酰胺显示出比​​ β-丙氨酸和 GABA 衍生物更高的活性。该活性与相应的牛磺酸衍生物相当。N,N-邻苯二甲酰甘氨酸酰胺在大鼠口服给药后在 MES 测试中也有活性。在皮下注射戊四唑的癫痫阈值试验中未发现显着活性。N的ED50，N-邻苯二甲酰-甘氨酸乙酰胺 (4b) 在 MES 试验中对小鼠腹膜内给药后的浓度为 19.1 mg/kg。在摩尔基础上，这种活性与苯妥英的活性相当，在转棒试验中几乎没有毒性。总之，N,N-邻苯二甲酰-甘氨酸酰胺可能代表有前景的抗癫痫药物。
• Hypolipidemic Activity of Phthalimide Derivatives IV: Further Chemical Modification and Investigation of the Hypolipidemic Activity of N-Substituted Imides
  作者：James M. Chapman、George H. Cocolas、I.H. Hall

  DOI：10.1002/jps.2600721127

  日期：1983.11

  A further investigation of N-substituted derivatives of phthalimide for hypolipidemic activity has revealed that the chain length, as well as the type of substitution on the N-alkyl chain of phthalimide is critical for biological activity. In these studies the hypolipidemic activity was not improved by extending the chain length beyond five carbon atoms in the alkyl and alkanoic acid series. Imido

  对邻苯二甲酰亚胺的N-取代衍生物进行降血脂活性的进一步研究表明，邻苯二甲酰亚胺的链长以及N-烷基链上的取代类型对于生物学活性至关重要。在这些研究中，通过将烷基和链烷酸系列中的碳原子长度延伸超过五个碳原子，并不能改善降血脂活性。除链烷酸，甲基酮和烷基以外的亚氨基氮取代基引起降血脂活性的降低，例如羟基，氨基，羟甲基或甲乙氧基。除了1-N-邻苯二甲酰亚胺基丁-3-酮半脲以外，将侧链的酮基还原为醇以及形成酮基的衍生物没有改善降血脂活性。该化合物表现出比邻苯二甲酰亚胺和1-N-邻苯二甲酰亚胺基丁三-3-酮改善的降胆固醇活性。邻苯二甲酰亚胺的芳族部分的3-位被氨基或硝基取代，以及用吡啶或环己基环取代苯环，导致降血脂活性降低。
• Proteasome inhibitors and methods of using the same
  申请人：Bernadini Raffaella

  公开号：US20050107307A1

  公开（公告）日：2005-05-19

  The present invention provides boronic acid compounds, boronic esters, and compositions thereof that can modulate apoptosis such as by inhibition of proteasome activity. The compounds and compositions can be used in methods of inducing apoptosis and treating diseases such as cancer and other disorders associated directly of indirectly with proteasome activity.

  本发明提供了硼酸化合物、硼酸酯及其组合物，可以通过抑制蛋白酶体活性等方式调节细胞凋亡。这些化合物和组合物可以用于诱导细胞凋亡并治疗癌症等疾病，以及与蛋白酶体活性直接或间接相关的其他疾病。
• Alicyclic-amine-substituted 4-carboxamido-benzimidazoles as parp-inhibitors and antioxidants
  申请人：Hideg Kalman

  公开号：US20070072912A1

  公开（公告）日：2007-03-29

  Compounds of the formula (I) and their pharmaceutically acceptable or technically applicable acid salts—where in the formula R 1 represents hydrogen, C (1-4) alkyl or C (1-4) alkoxy R 2 represents hydrogen, C (1-4) alkyl, carboxyl, C (1-4) alkoxycarbonyl, carboxamido, aryl or hetero-aryl R 3 represents hydrogen, C (1-4) alkyl, aryl-methylene, or aryl, Y is a valency bond, a straight or branched chain C (1-4) alkene, a carbonyl-amino-C (1-4) alkene, or a —S—(CH 2 ) m — group, where all alkene groups above may be spaced by an arylene group, n represents zero or the integer 1 m represents the integer 1, 2 or 3 Q represents hydrogen, hydroxyl or the oxygen radical (0) or together with the N atom of the adjacent ring forms a +N=O (oxoimmonium) group Z represents a single or double bond and their pharmaceutically acceptable or technically useful salts, processes for their preparation and their biological use as PARP inhibitors and antioxidants.

  公式（I）的化合物及其药学上可接受或技术上适用的酸盐——其中在公式中，R1代表氢，C（1-4）烷基或C（1-4）烷氧基；R2代表氢，C（1-4）烷基，羧基，C（1-4）烷氧羰基，羧酰胺基，芳基或杂环芳基；R3代表氢，C（1-4）烷基，芳基-亚甲基或芳基；Y是一个价键，一条直链或支链C（1-4）烯烃，一个羰基-氨基-C（1-4）烯烃，或一个—S—（CH2）m—基团，其中上述所有烯烃基团可以由一个芳基基团间隔；n代表零或整数1；m代表整数1、2或3；Q代表氢，羟基或氧基（0）或与相邻环的N原子一起形成+ N = O（氧代亚氨基）基团；Z代表单键或双键及其药学上可接受或技术上有用的盐，制备它们的过程以及它们作为PARP抑制剂和抗氧化剂的生物学用途。
• PROTEASOME INHIBITORS AND METHODS OF USING THE SAME
  申请人：Bernardini Raffaella

  公开号：US20090291918A1

  公开（公告）日：2009-11-26

  The present invention provides boronic acid compounds, boronic esters, and compositions thereof that can modulate apoptosis such as by inhibition of proteasome activity. The compounds and compositions can be used in methods of inducing apoptosis and treating diseases such as cancer and other disorders associated directly of indirectly with proteasome activity.

  本发明提供了硼酸化合物、硼酸酯及其组合物，可以调节细胞凋亡，例如通过抑制蛋白酶体活性。这些化合物和组合物可以用于诱导细胞凋亡和治疗癌症及其他与蛋白酶体活性直接或间接相关的疾病。