D-alanine n-propylamide | 63276-11-9

• 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: D-alanine n-propylamide
• 英文别名: (2R)-2-amino-N-propylpropanamide
• CAS: 63276-11-9
• 化学式: C₆H₁₄N₂O
• 分子量: 130.19
• InChiKey: ZTZLBRIYZPKLSX-RXMQYKEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  55.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  D-alanine n-propylamide 在 盐酸 、 TEA 、 N,N'-二环己基碳二亚胺 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 为溶剂， 生成 (S)-2-Propionylamino-N-((R)-1-propylcarbamoyl-ethyl)-propionamide
  参考文献：
  名称：

  Effect of stereochemistry on the transport of Aca-linked β-turn peptidomimetics across a human intestinal cell line

  摘要：

  Transcellular transport is one of the most important barriers facing the development of new therapeutic agents. However, little is known about the specific effects of structure and particularly stereochemistry on cell permeability. An attractive in vitro model has been developed for the direct assessment of cell transport, using the immortalized human epithelial cell line, Caco-2. The present study assesses the effects of stereochemistry on transport in a commonly used beta-turn model system. Thus, L,L- and L,D-Ala-Ala were cyclized with aminocaproic acid, resulting in macrocycles in which the dipeptides correspond to the i + 1 and i + 2 positions of a beta-turn. The transport of these dipeptides across a Caco-2 cell monolayer was determined, along with corresponding acyclic models (L,L- and L,D-CH3CH2C(0)-Ala-Ala-n-Pr). The transport studies were carried out in the presence and absence of verapamil, a known inhibitor of the apically polarized efflux system present in Caco-2 cells. Both apical-->basolateral and basolateral-->apical transport were measured. Measurements made in the presence of verapamil showed that the cyclic peptides experienced a ca. 4-5-fold difference in intrinsic flux depending on stereochemistry, with the L,D isomer being transported at a higher rate. These differences disappeared in the acyclic cases examined (permeability coefficient ratios of the L,D/L,L isomers were 1.04-1.13). These observations are discussed in terms of the conformations and hydrogen-bonding characteristics of the compounds as determined by NMR spectroscopy. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(97)00115-6
• 作为产物：
  描述：

  ((R)-1-Propylcarbamoyl-ethyl)-carbamic acid tert-butyl ester 在 盐酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 生成 D-alanine n-propylamide
  参考文献：
  名称：

  Effect of stereochemistry on the transport of Aca-linked β-turn peptidomimetics across a human intestinal cell line

  摘要：

  Transcellular transport is one of the most important barriers facing the development of new therapeutic agents. However, little is known about the specific effects of structure and particularly stereochemistry on cell permeability. An attractive in vitro model has been developed for the direct assessment of cell transport, using the immortalized human epithelial cell line, Caco-2. The present study assesses the effects of stereochemistry on transport in a commonly used beta-turn model system. Thus, L,L- and L,D-Ala-Ala were cyclized with aminocaproic acid, resulting in macrocycles in which the dipeptides correspond to the i + 1 and i + 2 positions of a beta-turn. The transport of these dipeptides across a Caco-2 cell monolayer was determined, along with corresponding acyclic models (L,L- and L,D-CH3CH2C(0)-Ala-Ala-n-Pr). The transport studies were carried out in the presence and absence of verapamil, a known inhibitor of the apically polarized efflux system present in Caco-2 cells. Both apical-->basolateral and basolateral-->apical transport were measured. Measurements made in the presence of verapamil showed that the cyclic peptides experienced a ca. 4-5-fold difference in intrinsic flux depending on stereochemistry, with the L,D isomer being transported at a higher rate. These differences disappeared in the acyclic cases examined (permeability coefficient ratios of the L,D/L,L isomers were 1.04-1.13). These observations are discussed in terms of the conformations and hydrogen-bonding characteristics of the compounds as determined by NMR spectroscopy. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(97)00115-6

文献信息

• Anti-ulcer polypeptides containing L-aspartic acid and intermediates
  申请人：G. D. Searle & Co.

  公开号：US04012367A1

  公开（公告）日：1977-03-15

  This invention encompasses novel tetrapeptide amides and their intermediates containing an L-aspartic acid residue. These peptides are inhibitors of gastric acid secretion and therefore useful in the treatment of ulcers.

  这项发明涵盖了含有L-天冬氨酸残基的新型四肽酰胺及其中间体。这些肽是胃酸分泌抑制剂，因此在溃疡治疗中有用。
• DISULFIDE BOND CONTAINING COMPOUNDS AND USES THEREOF
  申请人：THE UNIVERSITY OF QUEENSLAND

  公开号：US20200207810A1

  公开（公告）日：2020-07-02

  There is provided a range of novel disulfide bond containing compounds. These disulfide bond containing compounds can be used in a variety of applications such as solid phase peptide synthesis, solid phase organic synthesis, formation of dendrimers, formation of macromolecules and formation cyclic peptides; and as a component of a delivery vehicle with a bioactive molecule.
• US4012367A
  申请人：——

  公开号：US4012367A

  公开（公告）日：1977-03-15
• [EN] PTEFB-INHIBITOR-ADC<br/>[FR] CONJUGUÉ ANTICORPS-MÉDICAMENT (ADC) INHIBITEUR DE PTEFB
  申请人：BAYER PHARMA AG

  公开号：WO2017060322A2

  公开（公告）日：2017-04-13

  The invention relates to novel conjugates of a binder or a derivative thereof with one or more molecules of an active component, wherein the active component is a CDK9 kinase inhibitor, which is conjugated to the binder via a linker Z as described and defined herein, and methods for their preparation, their use for the treatment and/or prophylaxis of disorders, in particular of hyper-proliferative disorders.