H-D-Orn(Z)-OMe | 352274-96-5

• 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: H-D-Orn(Z)-OMe
• 英文别名: N^δ-Cbz-D-ornithine-OMe；(R)-methyl 2-amino-5-(((benzyloxy)carbonyl)amino)pentanoate；H-D-Orn(z)-ome hcl；methyl (2R)-2-amino-5-(phenylmethoxycarbonylamino)pentanoate
• CAS: 352274-96-5
• 化学式: C₁₄H₂₀N₂O₄
• 分子量: 280.324
• InChiKey: BJNJTVSXZUTHRA-GFCCVEGCSA-N

物化性质

• 沸点：
  433.0±45.0 °C(Predicted)
• 密度：
  1.162±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  90.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  H-D-Orn(Z)-OMe 在 barium hydroxide octahydrate 、 palladium 10% on activated carbon 、 氢气 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 三乙胺 、 N,N-二异丙基乙胺 、 potassium iodide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成
  参考文献：
  名称：

  Synthesis and antibacterial activity of conjugates between norfloxacin and analogues of the siderophore vanchrobactin

  摘要：

  From synthetic functionalized analogues of vanchrobactin, a siderophore produced by the fish pathogenic bacteria Vibrio anguillarum serotype O2, several vanchrobactin analogues-norfloxacin conjugates were obtained and their antimicrobial activities against the wild-type and mutant strains of Vibrio anguillarum serotype O2 have been determined. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.10.028
• 作为产物：
  描述：

  甲醇 、 N-叔丁氧羰基-N'-苄氧羰基-D-鸟氨酸 反应 24.0h， 以98%的产率得到H-D-Orn(Z)-OMe
  参考文献：
  名称：

  5-(Tryptophyl)amino-1,3-dioxoperhydropyrido[1,2-c]pyrimidine-Based Potent and Selective CCK₁ Receptor Antagonists:  Structure−Activity Relationship Studies on the Substituent at N2-Position

  摘要：

  To establish structure-activity relationships a new series of analogues of the highly potent and selective CCK1 receptor antagonist (4aS,5R)-2-benzyl-5-(N-Boc-tryptophyl)amino-1,3-dioxoperhydropyrido[1,2-c]-pyrimidine (1a) modified at N2-position of the central scaffold has been prepared and evaluated as CCK receptor ligands. With this aim the N2-benzyl group has been replaced by methyl, cyclohexyl, aromatic groups, 1-phenylethyl, and 1-carboxy-2-phenylethyl group. Then, substituents with different electronic and steric properties were introduced into different positions of the phenyl group of analogues 19a and 19b. The results of the CCK receptor binding and in vitro functional activity evaluation suggest the importance of the lipophilic character and an appropriate spatial orientation of the moiety linked at the N2-position of the 1,3-dioxoperhydropyrido[1,2-c]pyrimidine template for potent and selective binding and antagonist activity at CCK1 receptor subtype. The 2-cyclohexyl and (2S)-1-naphthyl derivatives 18a and (2S)-20a have emerged as more potent and selective CCK1 receptor antagonists than the lead compound 1a. Additionally, the results confirm the (4aS,5R)stereochemistry at the central bicyclic skeleton as an essential structural requirement for potent binding to this receptor subtype.

  DOI：

  10.1021/jm010813d

文献信息

• Human adam-10 inhibitors
  申请人：Brown S. David

  公开号：US20090143386A1

  公开（公告）日：2009-06-04

  The present invention provides compounds useful for inhibiting the ADAM-10 protein. Such compounds are useful in the in vitro study of the role of ADAM-10 (and its inhibition) in biological processes. The present invention also comprises pharmaceutical compositions comprising one or more ADAM-10 inhibitors according to the invention in combination with a pharmaceutically acceptable carrier. Such compositions are useful for the treatment of cancer, arthritis, and diseases related to angiogenesis. Correspondingly, the invention also comprises methods of treating forms of cancer, arthritis, and diseases related to angiogenesis in which ADAM-10 plays a critical role. The invention also provides methods for making bis-aryl ether sulfonyl chlorides and ADAM-10 modulators therefrom.

  本发明提供了用于抑制ADAM-10蛋白的化合物。这些化合物在体外研究ADAM-10（及其抑制）在生物过程中的作用方面非常有用。本发明还包括与一种或多种本发明的ADAM-10抑制剂结合的药学上可接受的载体组成的制药组合物。这样的组合物在治疗癌症、关节炎和与血管生成相关的疾病方面非常有用。相应地，本发明还包括治疗癌症、关节炎和与血管生成相关的疾病的方法，其中ADAM-10发挥关键作用。本发明还提供制备双芳基醚磺酰氯和ADAM-10调节剂的方法。
• Stereochemical Effects on the Antimicrobial Properties of Tetrasubstituted 2,5-Diketopiperazines
  作者：Thomas M. Grant、David Rennison、Alexandra L. Krause、Sonya Mros、Scott A. Ferguson、Gregory M. Cook、Alan Cameron、Homayon J. Arabshahi、Margaret A. Brimble、Patrick Cahill、Johan Svenson

  DOI：10.1021/acsmedchemlett.1c00683

  日期：2022.4.14

  the treatment of persistent microbial infections. In the current study, we investigate five cyclic N-alkylated amphiphilic 2,5-diketopiperazines against 15 different strains of bacteria and fungi, including drug-resistant clinical isolates. Several of the 2,5-diketopiperazines displayed activities similar or superior to antibiotics currently in clinical use, with activities coupled to both the cationic

  抗生素耐药性是现代我们面临的迫在眉睫的健康危机，迫切需要新药来应对这一日益严重的问题。抗菌肽的合成模拟物最近已成为一类很有前途的化合物，可用于治疗持续性微生物感染。在目前的研究中，我们调查了五个循环N-烷基化两亲性 2,5-二酮哌嗪对 15 种不同的细菌和真菌菌株，包括耐药临床分离株。几种 2,5-二酮哌嗪显示出与目前临床使用的抗生素相似或优于抗生素的活性，其活性与阳离子和疏水取代基结合。制备了先导肽的所有可能的立体异构体，并通过一维和二维核磁共振光谱、溶液动力学和膜相互作用模型研究了立体化学和两亲性的影响。溶液结构和膜相互作用电位的明显差异解释了每种立体异构体的生物活性和物理化学性质的差异。
• Solution-Phase-Peptide Synthesis without Purification of Column Chromatography and Recrystallization by Protecting Amino Acid Esters with Phosphinyl Chloride
  作者：Guigen Li、Guanghui An、Wei Zhou、Xiaokang Xu、Yi Pan

  DOI：10.3987/com-14-s(k)99

  日期：——

  Biphenyl phosphinyl chloride (Bpp-Cl) has been successfully applied for the amino acid GAP (Group-Assisted Purification) protection. The resulting N-protected amino acid esters have been readily converted into the corresponding amino acids and peptides through GAP operation. Biphalin, enkephalin derivatives and the fragments of surfaxin have also been synthesized via GAP work-up by avoiding column chromatography. The GAP protecting group (Bpp) can be recovered and can implement the former phosphonyl groups in peptide synthesis.
• Vanchrobactin: absolute configuration and total synthesis
  作者：Raquel G. Soengas、Cristina Anta、Alfonso Espada、Rosa M. Nieto、Marta Larrosa、Jaime Rodríguez、Carlos Jiménez

  DOI：10.1016/j.tetlet.2007.02.125

  日期：2007.4

  The stereochemistry of vanchrobactin, a siderophore produced by the bacterial fish pathogen Vibrio anguillarum serotype O2, was elucidated by chiral capillary electrophoresis analysis and total synthesis as N-[N'-(2,3-dihydroxybenzoyl)-D-arginyl]-L-serine. (c) 2007 Elsevier Ltd. All rights reserved.
• US7498358B2
  申请人：——

  公开号：US7498358B2

  公开（公告）日：2009-03-03