2-(fluoromethyl)-5-iodo-2-phthalimidopentanenitrile | 80931-00-6

• 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: 2-(fluoromethyl)-5-iodo-2-phthalimidopentanenitrile
• 英文别名: 2-fluoromethyl-2-phthalimido-5-iodo-valeronitrile；2-fluoromethyl-2-phthalimido-5-iodopentanenitrile；2-(1,3-dioxoisoindol-2-yl)-2-(fluoromethyl)-5-iodopentanenitrile
• CAS: 80931-00-6
• 化学式: C₁₄H₁₂FIN₂O₂
• 分子量: 386.164
• InChiKey: CLFSAHQFWINQID-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  61.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-邻苯二甲酰亚胺基丙二酸二乙酯 、 2-(fluoromethyl)-5-iodo-2-phthalimidopentanenitrile 在 potassium tert-butylate 作用下， 生成 ethyl 2-(carbethoxy)-6-cyano-2,6-diphthalimido-7-fluoroheptanoate
  参考文献：
  名称：

  2-(4-Amino-4-carboxybutyl)aziridine-2-carboxylic acid. A potent irreversible inhibitor of diaminopimelic acid epimerase. Spontaneous formation from .alpha.-(halomethyl)diaminopimelic acids

  摘要：

  2-(4-Amino-4-carboxybutyl)aziridine-2-carboxylic acid (3) (aziridino-DAP) was identified as the product of spontaneous hydrolysis of alpha-(halomethyl)diaminopimelic acids (alpha-halomethyl-DAPs) 2a-c. Under physiological conditions, 3 is an extremely potent irreversible inhibitor of the bacterial enzyme diaminopimelic acid epimerase (DAP-epimerase; EC 5.1.1.7). This unusual mode of action of an alpha-halomethyl amino acid with a non-pyridoxal enzyme is investigated. Synthesis and characterization of 2a-c and 3, kinetics of spontaneous formation of 3 from alpha-halomethyl-DAPs, and kinetics of enzyme inhibition by both 3 and by alpha-halomethyl-DAPs are reported.

  DOI：

  10.1021/jm00170a018
• 作为产物：
  描述：

  2-fluoromethyl-2-phthalimido-5-hydroxy-valeronitrile 在 吡啶 、 sodium iodide 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 15.0h， 生成 2-(fluoromethyl)-5-iodo-2-phthalimidopentanenitrile
  参考文献：
  名称：

  2-(4-Amino-4-carboxybutyl)aziridine-2-carboxylic acid. A potent irreversible inhibitor of diaminopimelic acid epimerase. Spontaneous formation from .alpha.-(halomethyl)diaminopimelic acids

  摘要：

  2-(4-Amino-4-carboxybutyl)aziridine-2-carboxylic acid (3) (aziridino-DAP) was identified as the product of spontaneous hydrolysis of alpha-(halomethyl)diaminopimelic acids (alpha-halomethyl-DAPs) 2a-c. Under physiological conditions, 3 is an extremely potent irreversible inhibitor of the bacterial enzyme diaminopimelic acid epimerase (DAP-epimerase; EC 5.1.1.7). This unusual mode of action of an alpha-halomethyl amino acid with a non-pyridoxal enzyme is investigated. Synthesis and characterization of 2a-c and 3, kinetics of spontaneous formation of 3 from alpha-halomethyl-DAPs, and kinetics of enzyme inhibition by both 3 and by alpha-halomethyl-DAPs are reported.

  DOI：

  10.1021/jm00170a018
• 作为试剂：
  描述：

  碘化钠 、 2-fluoromethyl-2-phthalimido-5-benzyloxy-valeronitrile 、 碳酸氢钠 、 disodium;dioxido-oxo-sulfanylidene-λ6-sulfane 、 在 Chlorotrimethylsilyl 、 乙醚 、 magnesium sulfate 、 三乙胺 、 水 、 2-fluoromethyl-2-phthalimido-5-hydroxy-valeronitrile 、 2-(fluoromethyl)-5-iodo-2-phthalimidopentanenitrile 、 iodotrimethylsilyl 、 florisil 作用下， 以 乙腈 、 水 为溶剂， 反应 33.83h， 以gives 22 g of 2-fluoromethyl-2-phthalimido-5-iodopentanenitrile as an oil的产率得到2-(fluoromethyl)-5-iodo-2-phthalimidopentanenitrile
  参考文献：
  名称：

  2-Halomethyl derivatives of 2-amino acids

  摘要：

  2-(氟甲基或氯甲基)-2,5-二氨基戊酸，2-(氟甲基或氯甲基)-2,6-二氨基己酸和2-氟甲基-2-氨基-5-胍基戊酸及其某些衍生物是鸟氨酸脱羧酶的抑制剂。本文还描述了制备这些化合物和衍生物的方法。

  公开号：

  US04866206A1

文献信息

• Process for preparing fluorinated amino-nitriles
  申请人：Merrell Toraude et Compagnie

  公开号：US04405530A1

  公开（公告）日：1983-09-20

  Certain .alpha.-(fluoromethyl or difluoromethyl)-.alpha.-aminoacetonitriles are prepared by treating the appropriate .alpha.-(fluoromethyl or difluoromethyl) ketimine magnesium halide with hydrogen cyanide or with an alkali metal cyanide or ammonium cyanide and a proton source. The products are useful as intermediates for making .alpha.-(fluoromethyl or difluoromethyl)-.alpha.-amino acids having pharmacological activity.

  某些α-(氟甲基或二氟甲基)-α-氨基乙腈是通过将相应的α-(氟甲基或二氟甲基)酮亚胺镁卤化物与氢氰酸或与碱金属氰化物、氰化铵及质子源反应制备而成。这些产物作为中间体，可用于合成具有药理活性的α-(氟甲基或二氟甲基)-α-氨基酸。
• Method of treating benign prostatic hypertrophy
  申请人：Merrell-Toraude et Cie

  公开号：US04330559A1

  公开（公告）日：1982-05-18

  There is described a method for treating benign prostatic hypertrophy comprising the administration of 2,5-di-amino-2-(mono-,di-, or trifluoromethyl)pentanoic acid or derivative thereof.

  描述了一种治疗良性前列腺肥大的方法，包括给予2,5-二氨基-2-(单、二、或三氟甲基)戊酸或其衍生物。
• 2-halomethyl derivatives of 2-amino acids
  申请人：Merrell Dow France et Cie

  公开号：US04743691A1

  公开（公告）日：1988-05-10

  2-(Fluoromethyl or chloromethyl)-2,5-diaminopentanoic acid, 2-(fluoromethyl or chloromethyl)-2,6-diaminohexanoic acid, and 2-fluoromethyl-2-amino-5-guanidinopentanoic acid, and certain derivatives thereof, are inhibitors of ornithine decarboxylase. Methods of preparing the compounds and derivatives are also described.

  2-(氟甲基或氯甲基)-2,5-二氨基戊酸，2-(氟甲基或氯甲基)-2,6-二氨基己酸和2-氟甲基-2-氨基-5-胍基戊酸及其某些衍生物是鸟氨酸脱羧酶的抑制剂。本文还描述了制备这些化合物和衍生物的方法。
• Method of controlling tumor growth rate
  申请人：Marion Merrell et Compagnie C/O Merrell Pharmaceuticals Inc.

  公开号：US05614557A1

  公开（公告）日：1997-03-25

  .alpha.-Fluoromethyl- or .alpha.-difluoromethylornithine, and certain derivatives thereof, can be used alone or in combination with cytotoxic agents for the treatment of neoplastic diseases.

  .alpha.-氟甲基或.alpha.-二氟甲基鸟氨酸及其某些衍生物，可以单独或与细胞毒性药物联合使用，用于治疗恶性肿瘤疾病。
• Method for controlling fertility in mammals
  申请人：Merrell Toraude et Compagnie

  公开号：US04309442A1

  公开（公告）日：1982-01-05

  A method for preventing gestation in mammals comprising the administration of a 2,5-diamino-2-halomethylpentanoic acid or derivative thereof.

  一种预防哺乳动物妊娠的方法，包括给予2,5-二氨基-2-卤代甲基戊酸或其衍生物的治疗。