D-青霉胺甲酯 | 29913-83-5

• 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
• 中文名称: D-青霉胺甲酯
• 英文名称: D-penicillamine methyl ester
• 英文别名: 3,3-dimethyl-D-cysteine methyl ester；Penicillamine methyl ester；methyl (S)-penicilamine；D-Penicillamin-methylester；D-α-Amino-β-mercapto-isovaleriansaeure-methylester；(S)-methyl 2-amino-3-mercapto-3-methylbutanoate；methyl (2S)-2-amino-3-methyl-3-sulfanylbutanoate
• CAS: 29913-83-5
• 化学式: C₆H₁₃NO₂S
• 分子量: 163.241
• InChiKey: FIXGPNLTDAUQQF-BYPYZUCNSA-N

物化性质

• 沸点：
  207.9±30.0 °C(Predicted)
• 密度：
  1.094±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  10
• 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：
  53.3
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  D-青霉胺甲酯 在 N-甲基吗啉 、 碘 作用下， 以 四氢呋喃 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.33h， 生成 methyl 13α-<<(1,1-dimethylethoxy)carbonyl>amino>-3,3-14,14-tetramethyl-6,12-dioxo-7-(phenylmethyl)-1,2-dithia-5,11-diazacyclotetradecane-(4R)-4α-carboxylate
  参考文献：
  名称：

  Analogs of the .delta. opioid receptor selective cyclic peptide [cyclic][2-D-penicillamine,5-D-penicillamine]-enkephalin: 2',6'-dimethyltyrosine and Gly3-Phe4 amide bond isostere substitutions

  摘要：

  In order to develop systemically-active opioid peptides, the delta-selective, opioid pentapeptide [D-Pen2,D-Pen5]-enkephalin (DPDPE) was modified by esterification and by substitution of 2,6-dimethyltyrosine for tyrosine to yield 4. Compound 4 was on the order of 8- and 800-fold more active than DPDPE in both delta and mu-opioid radioligand binding assays, respectively, in rat neural membrane suspensions. Compound 4 was considerably more potent than DPDPE at inhibiting contractions of electrically-stimulated mouse vas deferens in vitro, and this effect was very sensitive to naltrindole, a delta-selective opioid antagonist. These observations can be taken as indication that 4 exerts its effects through delta-opioid receptors. This interpretation is supported by the finding that the EC50 value of 4 derived in the smooth muscle assay is very similar to that derived in NG108-15 neuroblastoma cells, a preparation devoid of mu-receptors. Unlike DPDPE, 4 exhibited significant, naloxone-sensitive, antinociceptive activity when administered systemically, as measured by inhibition of phenylbenzquinone-induced stretching in mice (ED50 = 2.1 mg/kg). Compound 4 also displayed significant antinociceptive activity following systemic administration as measured by its action in mice to increase latencies for tail withdrawal from radiant heat (ED50 = 50 mg/kg). Compound 4 did not produce morphine-like discriminative stimulus effects in rats trained to discriminate 3.0 mg/kg morphine from vehicle at doses ranging from 30 to 120 mg/kg. This observation can be interpreted as indication that within this dosage range there is an absence of morphine-like subjective effects. Physical dependence, however, could be induced in mice at higher doses of 4 under a progressively-graded, 4-day dose regimen. Congeners of 4 with amide bond surrogates for the Gly-Phe amide bond (oxymethylene, trans-double bond, and bismethylene isosteres) in the cyclic core of DPDPE were prepared in an attempt to increase the antinociceptive activity of 4. While some of the were active in the in vitro assays, they did not display significant antinociceptive activity following systemic administration. The preparation of all the compounds was accomplished by solution-phase methods. The which might underlie the biological and systemic activity of 4 are discussed.

  DOI：

  10.1021/jm00094a002
• 作为产物：
  描述：

  D-青霉胺 生成 D-青霉胺甲酯
  参考文献：
  名称：

  跨环反应合成青霉素环系的尝试

  摘要：

  试图通过实现 3D-carbomethoxy-N-chloro-2,2-dimethyl-5-oxoperhydro-6L-phthalimido-1,4-thiazepine 砜的跨环环化来实现青霉素环系统的新合成。然而，获得的产物是由环裂解和消除反应产生的产物。

  DOI：

  10.1139/v72-353

文献信息

• Analgesic Compounds, Compositions, and Uses Thereof
  申请人：Mannion James C.

  公开号：US20110224269A1

  公开（公告）日：2011-09-15

  The invention relates to compounds, compositions, and methods for diminishing pain in a subject in need thereof comprising administering the compounds and compositions herein described.

  这项发明涉及化合物、组合物和方法，用于减轻需要的受试者的疼痛，包括给予所述的化合物和组合物。
• CYCLOSPORIN ANALOGS
  申请人：Allergan, Inc.

  公开号：US20170029469A1

  公开（公告）日：2017-02-02

  Disclosed herein are novel analogs of cyclosporin, pharmaceutical compositions containing them, and methods for their use in the treatment of dry eye and other conditions.

  本文披露了环孢霉素的新型类似物，包含它们的药物组合物，以及它们在治疗干眼症和其他疾病中的使用方法。
• The synthesis and conformational analysis of a pair of diastereoisomeric cyclic peptides with cis and transamide bonds, respectively
  作者：Sabrina Cumberbatch、Michael North、Guiseppe Zagotto

  DOI：10.1039/c39930000641

  日期：——

  N-Protected, conformationally constrained, eight-membered ring containing cyclic dipeptides derived from methyl cyclo-[(R)-cysteinyl-(R)-penicillamine] contain a cis amide bond, whilst the corresponding peptides derved from cyclo-[(R)-cysteinyl-(S)-penicillamine] contain a trans amide bond.

  Ñ -protected，构象受限，含有来自甲基环衍生的环二肽八元环- [（[R）-cysteinyl-（[R ）青霉胺]含有顺式酰胺键，而从环derved相应肽- [（[R ）-半胱氨酰基-（S）-青霉胺]含有反式酰胺键。
• A compact fluorescence/circular dichroism dual-modality probe for detection, differentiation, and detoxification of multiple heavy metal ions via bond-cleavage cascade reactions
  作者：Junwei Chen、Na Wang、Hongjuan Tong、Chao Song、Huijuan Ma、Yajun Zhang、Feng Gao、Huan Xu、Wei Wang、Kaiyan Lou

  DOI：10.1016/j.cclet.2021.05.047

  日期：2021.12

  Selective detection of multiple analytes in a compact design with dual-modality and theranostic features presents great challenges. Herein, we wish to report a coumarin-thiazolidine masked D-penicillamine based dual-modality fluorescent probe COU-DPA-1 for selective detection, differentiation, and detoxification of multiple heavy metal ions (Ag+, Hg2+, Cu2+). The probe shows divergent fluorescence

  在具有双重模式和诊断学特征的紧凑设计中选择性检测多种分析物提出了巨大的挑战。在此，我们希望报告一种香豆素-噻唑烷掩蔽的D-青霉胺双模态荧光探针COU-DPA-1，用于多种重金属离子（Ag +，Hg 2 +，Cu 2+）的选择性检测，区分和解毒。。该探针通过不同的键裂解级联反应（金属离子促进了CS裂解和在两个不同裂解位点的水解）显示出不同的荧光（FL）/圆二色性（CD）反应：FL“关闭”和CD“开启”对于Ag +（无水解），对于Hg 2 +，FL为“开启”，CD为“关闭”（亚胺水解）和过量铜2+（内酯和亚胺水解）的FL“自阈值比率”和CD“关闭” ，提供了荧光/ CD双峰探针的第一个示例，适用于多种具有互补性的物质回应。此外，键断裂级联反应还导致形成D-青霉胺重金属离子络合物，用于潜在的解毒治疗。
• Method for inducing cell death with carbonyl scavengers
  申请人：Wondrak T. Georg

  公开号：US20050197400A1

  公开（公告）日：2005-09-08

  Carbonyl scavengers, which have been recognized for their ability to react with reactive carbonyl species, have been implicated as agents that can accelerate or induce the death of abnormal cells without having a parallel effect on normal cells. As such, they are useful therapeutic agents in cases where the acceleration or induction of cell death is desirable, such as in cells where the normal apoptotic pathways have been disrupted and where hyperproliferative cell growth occurs.

  羰基清除剂，因其能够与反应性羰基物种反应而被认为是能够加速或诱导异常细胞死亡而不对正常细胞产生平行影响的剂量。因此，在需要加速或诱导细胞死亡的情况下，如正常凋亡途径被破坏并出现过度增殖的细胞中，它们是有用的治疗剂量。