(2S,4R)-4-[[[[2-[[叔丁氧羰基]氨基]乙基]氨基]羰基]氧基]-1,2-吡咯烷二甲酸 1-(9H-芴-9-基甲基)酯 | 187223-15-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 中文名称: (2S,4R)-4-[[[[2-[[叔丁氧羰基]氨基]乙基]氨基]羰基]氧基]-1,2-吡咯烷二甲酸 1-(9H-芴-9-基甲基)酯
• 中文别名: (2S,4R)-4-[[[[2-[[叔丁氧羰基]氨基]乙基]氨基]羰基]氧基]-1,2-吡咯烷二甲酸1-(9H-芴-9-基甲基)酯；Fmoc-4-(Boc-2-氨乙基-氨甲酰)-L-羟脯氨酸
• 英文名称: Fmoc-(2S,4R)-(4-OCO-NH-CH2-CH2-NH-Boc)-Pro-OH
• 英文别名: Fmoc-(2S,4R)-Pro(4-OCO-NH-CH2-CH2-NH-Boc)-OH；Fmoc-Hyp(Bom)-OH；(2S,4R)-1-(9H-fluoren-9-ylmethoxycarbonyl)-4-[2-[(2-methylpropan-2-yl)oxycarbonylamino]ethylcarbamoyloxy]pyrrolidine-2-carboxylic acid
• CAS: 187223-15-0
• 化学式: C₂₈H₃₃N₃O₈
• 分子量: 539.585
• InChiKey: PFVAFJSUWCTINJ-HXOBKFHXSA-N

物化性质

• 沸点：
  749.0±60.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  39
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  144
• 氢给体数：
  3
• 氢受体数：
  8

安全信息

• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  (2S,4R)-4-[[[[2-[[叔丁氧羰基]氨基]乙基]氨基]羰基]氧基]-1,2-吡咯烷二甲酸 1-(9H-芴-9-基甲基)酯 在 三氟乙酸 作用下， 反应 1.0h， 以98%的产率得到Fmoc-(2S,4R)-(4-OCO-NH-CH2-CH2-NH2)-Pro-OH
  参考文献：
  名称：

  A Novel Somatostatin Mimic with Broad Somatotropin Release Inhibitory Factor Receptor Binding and Superior Therapeutic Potential

  摘要：

  A rational drug design approach, capitalizing on structure-activity relationships and involving transposition of functional groups from somatotropin release inhibitory factor (SRIF) into a reduced size cyclohexapeptide template, has led to the discovery of SOM230 (25), a novel, stable cyclohexapeptide somatostatin mimic that exhibits unique high-affinity binding to human somatostatin receptors (subtypes sst1-sst5). SOM230 has potent, long-lasting inhibitory effects on growth hormone and insulin-like growth factor-1 release and is a promising development candidate currently under evaluation in phase I clinical trials.

  DOI：

  10.1021/jm021093t
• 作为产物：
  描述：

  N-Fmoc-反式-4-羟基-L-脯氨酸甲酯 在 4-二甲氨基吡啶 、 sodium hydroxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 3.0h， 生成 (2S,4R)-4-[[[[2-[[叔丁氧羰基]氨基]乙基]氨基]羰基]氧基]-1,2-吡咯烷二甲酸 1-(9H-芴-9-基甲基)酯
  参考文献：
  名称：

  A Novel Somatostatin Mimic with Broad Somatotropin Release Inhibitory Factor Receptor Binding and Superior Therapeutic Potential

  摘要：

  A rational drug design approach, capitalizing on structure-activity relationships and involving transposition of functional groups from somatotropin release inhibitory factor (SRIF) into a reduced size cyclohexapeptide template, has led to the discovery of SOM230 (25), a novel, stable cyclohexapeptide somatostatin mimic that exhibits unique high-affinity binding to human somatostatin receptors (subtypes sst1-sst5). SOM230 has potent, long-lasting inhibitory effects on growth hormone and insulin-like growth factor-1 release and is a promising development candidate currently under evaluation in phase I clinical trials.

  DOI：

  10.1021/jm021093t

文献信息

• [EN] NOVEL PROCESS FOR THE PREPARATION OF PASIREOTIDE<br/>[FR] NOUVEAU PROCÉDÉ DE PRÉPARATION DE PASIRÉOTIDE
  申请人：BIOPHORE INDIA PHARMACEUTICALS PVT LTD

  公开号：WO2016207912A1

  公开（公告）日：2016-12-29

  The present invention relates to a novel process for the preparation of Pasireotide of formula 11 [Cyclo [Phe-4-(OCO-NH-CH2-CH2-NH2)) Pro}-Phg-DTrp-Lys-Tyr(Bzl)]]. The invention also relates to a novel intermediate compound of formula 8 and process thereof which is used for preparation of compound of formula 11.

  本发明涉及一种用于制备化学式11的帕西瑞肽的新型工艺。该发明还涉及一种化学式8的新型中间化合物及其制备工艺，该中间化合物用于制备化合物11。
• [EN] CYCLOHEXAPEPTIDES AS SELECTIVE SOMATOSTATIN SST5 RECEPTOR AGONISTS<br/>[FR] CYCLOHEXAPEPTIDES EN TANT QU'AGONISTES SÉLECTIFS DU RÉCEPTEUR DE LA SOMATOSTATINE SST5
  申请人：HEPTARES THERAPEUTICS LTD

  公开号：WO2020074926A1

  公开（公告）日：2020-04-16

  The disclosures herein relate to novel compounds of formula (1) : (1) and salts thereof, wherein W, X, Y, Z, m, n, q, R1, R2, R3, R4, R5 and R6 are defined herein, and their use in treating, preventing, ameliorating, controlling or reducing the risk of disorders associated with somatostatin receptors.

  本公开涉及式（1）的新化合物及其盐：（1），其中W、X、Y、Z、m、n、q、R1、R2、R3、R4、R5和R6在此处定义，并其在治疗、预防、改善、控制或减少与生长抑素受体相关的疾病风险方面的用途。
• [EN] PROCESS FOR PEPTIDE SYNTHESIS OF PEPTIDES CONTAINING A 4-HYDROXY-PROLINE SUBSTRUCTURE<br/>[FR] PROCEDE DE SYNTHESE PEPTIDIQUE CONTENANT UNE SOUS-STRUCTURE DE 4-HYDROXY-PROLINE
  申请人：NOVARTIS AG

  公开号：WO2004052817A1

  公开（公告）日：2004-06-24

  The present invention relates to processes for preparing peptides and to intermediates involved in such processes, e.g. a process for preparing a compound of formula (VIII) wherein R12 and R13 are as defined herein.

  本发明涉及制备肽的过程以及参与该过程的中间体，例如，制备式（VIII）化合物的过程，其中R12和R13如本文所定义。
• A Novel Somatostatin Mimic with Broad Somatotropin Release Inhibitory Factor Receptor Binding and Superior Therapeutic Potential
  作者：Ian Lewis、Wilfried Bauer、Rainer Albert、Nagarajan Chandramouli、Janos Pless、Gisbert Weckbecker、Christian Bruns

  DOI：10.1021/jm021093t

  日期：2003.6.1

  A rational drug design approach, capitalizing on structure-activity relationships and involving transposition of functional groups from somatotropin release inhibitory factor (SRIF) into a reduced size cyclohexapeptide template, has led to the discovery of SOM230 (25), a novel, stable cyclohexapeptide somatostatin mimic that exhibits unique high-affinity binding to human somatostatin receptors (subtypes sst1-sst5). SOM230 has potent, long-lasting inhibitory effects on growth hormone and insulin-like growth factor-1 release and is a promising development candidate currently under evaluation in phase I clinical trials.