Boc-S-(4-甲氧苄基)-D-青霉胺 | 106306-57-4

• 物质功能分类: 生物化工 - 生化试剂 - 氨基酸
• 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
• 中文名称: Boc-S-(4-甲氧苄基)-D-青霉胺
• 英文名称: Boc-^DPen(MBzl)-OH
• 英文别名: Boc-D-Pen(Mob)-OH；(2S)-3-[(4-methoxyphenyl)methylsulfanyl]-3-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoic acid
• CAS: 106306-57-4
• 化学式: C₁₈H₂₇NO₅S
• mdl: MFCD00076973
• 分子量: 369.482
• InChiKey: NEUHEEDQLRFEIM-AWEZNQCLSA-N

物化性质

• 熔点：
  108-115°C
• 沸点：
  523.2±50.0 °C(Predicted)
• 密度：
  1.168±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.555
• 拓扑面积：
  110
• 氢给体数：
  2
• 氢受体数：
  6

安全信息

• 危险等级：
  IRRITANT
• WGK Germany：
  3
• 危险类别：
  IRRITANT
• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  Boc-S-(4-甲氧苄基)-D-青霉胺 、 三氟乙酸 在 ice 、 三氟乙酸 、 二氯甲烷 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 H-beta,beta-Dimethyl-D-cys(pmeobzl)-OH
  参考文献：
  名称：

  Acyclic metalloprotease inhibitors

  摘要：

  该发明提供了公式如权利要求所述的化合物，或其光学异构体、对映异构体或立体异构体，或其药学上可接受的盐，或其生物可水解的酰胺、酯或亚酰胺，作为金属蛋白酶抑制剂。还公开了使用这些化合物或含有它们的药物组合物治疗由金属蛋白酶活性所特征的疾病、疾病和病情的方法和制药组合物。

  公开号：

  US06218389B1

文献信息

• Synthesis and biological property of .ALPHA.-human atrial natriuretic peptide analogs with a constrained or stereochemically modified cyclic moiety.
  作者：Yoshiharu MINAMITAKE、Mayumi FURUYA、Yasuo KITAJIMA、Maki TAKEHISA、Shoji TANAKA

  DOI：10.1248/cpb.38.1920

  日期：——

  Conformationally restricted analogs of α-human atrial natriuretic peptide (α-hANP) containing L- or D-penicillamine, or D-cysteine in place of cysteine residues at positions 7 and 23 were synthesized by the liquid phase procedure. Their biological properties in the assays of receptor binding and cyclic guanosine monophosphate (cGMP) accumulation employing rat vascular smooth muscle cells (VSMC), vasorelaxant activity using rat isolated aorta were evaluated. We found that the constrained and/or stereochemically altered ring moiety generally did not influence the receptor binding activity, however, cGMP accumulation and vasorelaxant activities were quite sensitive to conformational perturbation. Furthermore, a lack of correlation between cGMP acccumulation activity and vasorelaxant activity was observed. Dissociation between these activities was typical in the case of [DPen7, 23]-α-hANP(7-28), which showed quite weak vasorelaxant activity in spite of its full cGMP accumulation and receptor binding potencies. This result suggests that cGMP accumulation alone is not sufficient to promote AMP-induced vasorelaxation, and that the other second messenger (s) may mediate this activity.

  通过液相法合成了α-人心房钠尿肽（α-hANP）的构象限制性类似物，这些类似物在第7和23位氨基酸残基上分别含有L型或D型的青霉胺，或D型的半胱氨酸。我们评估了这些化合物的生物学特性，包括利用大鼠血管平滑肌细胞（VSMC）进行的受体结合试验和环磷酸鸟苷（cGMP）积累试验，以及使用大鼠离体主动脉进行的血管舒张活性试验。我们发现，受限制和/或立体化学改变的环结构通常不影响受体结合活性，然而，环磷酸鸟苷积累和血管舒张活性对构象扰动相当敏感。此外，我们观察到环磷酸鸟苷积累活性与血管舒张活性之间缺乏相关性。在这些活性之间表现出典型分离的是[DPen7, 23]-α-hANP(7-28)，尽管它具有完全的环磷酸鸟苷积累和受体结合效力，但其血管舒张活性相当弱。这一结果表明，仅环磷酸鸟苷的积累不足以促进ANP诱导的血管舒张，其他第二信使可能介导这一活性。
• A New Method for the Preparation of 3-Nitro-2-pyridinesulfenyl Chloride and One-Pot Syntheses of<i>N</i>(α)-<i>tert</i>-butoxycarbonyl-<i>S</i>-3-nitro-2-pyridinesulfenyl Derivatives of Cysteine and D-Penicillamine
  作者：Masaaki Ueki、Maki Honda、Yuki Kazama、Tsuyoshi Katoh

  DOI：10.1055/s-1994-25394

  日期：——

  3-Nitro-2-pyridinesulfenyl chloride was prepared by the reaction of benzyl 3-nitro-2-pyridyl sulfides with sulfuryl chloride. One-pot syntheses of N (α)- tert-butoxycarbonyl-S-3-nitro-2-pyridinesulfenyl derivatives of cysteine and D-penicillamine were accomplished using 4-methoxybenzyl 3-nitro-2-pyridyl sulfide.

  通过 3-硝基-2-吡啶苄基硫化物与硫酰氯的反应制备了 3-硝基-2-吡啶硫酰氯。使用 4-甲氧基苄基 3-硝基-2-吡啶硫化物完成了半胱氨酸和 D-青霉胺的 N (δ)- 叔丁氧羰基-S-3-硝基-2-吡啶亚磺酰基衍生物的一锅合成。
• Biological and Conformational Evaluation of Bifunctional Compounds for Opioid Receptor Agonists and Neurokinin 1 Receptor Antagonists Possessing Two Penicillamines
  作者：Takashi Yamamoto、Padma Nair、Neil E. Jacobsen、Vinod Kulkarni、Peg Davis、Shou-wu Ma、Edita Navratilova、Henry I. Yamamura、Todd W. Vanderah、Frank Porreca、Josephine Lai、Victor J. Hruby

  DOI：10.1021/jm100157m

  日期：2010.8.12

  Neuropathic pain states and tolerance to opioids can result from system changes in the CNS, such as up-regulation of the NK1 receptor and substance P, lead to antiopioid effects in ascending or descending pain-signaling pathways. Bifunctional compounds, possessing both the NK1 antagonist pharmacophore and the opioid agonist pharmacophore with delta-selectivity, could counteract these system changes to have significant analgesic efficacy without undesirable side effects. As a result of the introduction of cyclic and topological constraints with penicillamines, 2 (Tyr-cyclo[D-Pen-Gly-Phe-Per+Pro-Leu-Trp-NH-[3',5'-(CF3)(2)-Bzl]) was found as the best bifunctional compound with effective NK1 antagonist and potent opioid agonist activities, and 1400-fold delta-selectivity over the mu-receptor. The NMR structural analysis of 2 revealed that the relative positioning of the two connected pharmacophores as well as its cyclic and topological constraints might be responsible for its excellent bifunctional activities as well as its significant delta-opioid selectivity. Together with the observed high metabolic stability, 2 could be considered as a valuable research tool and possibly a promising candidate for a novel analgesic drug.
• Novel Opioid Peptide Derived Antagonists Containing (2<i>S</i>)-2-Methyl-3-(2,6-dimethyl-4-carbamoylphenyl)propanoic Acid [(2<i>S</i>)-Mdcp]
  作者：Animesh Ghosh、Jie Luo、Chen Liu、Grazyna Weltrowska、Carole Lemieux、Nga N. Chung、Yixin Lu、Peter W. Schiller

  DOI：10.1021/jm8004702

  日期：2008.9.25

  A synthesis of the novel tyrosine analogue (2S)-2-methyl-3-(2,6-dimethyl-4-carbamoylphenyl)propanoic acid [(2S)-Mdcp] (15) was developed. In (2S)-Mdcp, the amino and hydroxyl groups of 2',6'-dimethyltyrosine are replaced by a methyl and a carbamoyl group, respectively, and its substitution for Tyr(1) in opioid agonist peptides resulted in compounds showing antagonism at all three opioid receptors. The cyclic peptide (2S)Mdcp-c[D-Cys-Gly-Phe(pNO(2))-D-Cys]NH2 (1) Was a potent and selective mu antagonist, whereas (2S)-Mdcp-C[D-Pen-GIy-Phe(pF)-Pen]-Phe-OH (3) showed subnanomolar delta antagonist activity and extraordinary delta selectivity.
• SULFONYLAMINO SUBSTITUTED HYDROXAMIC ACID DERIVATIVES AS METALLOPROTEASE INHIBITORS
  申请人：THE PROCTER & GAMBLE COMPANY

  公开号：EP1009737A2

  公开（公告）日：2000-06-21