4-氨基-D-苯丙氨酸 | 102281-45-8

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 苯丙氨酸类衍生物
• 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: 4-氨基-D-苯丙氨酸
• 中文别名: D-4-氨基苯丙氨酸
• 英文名称: p-amino-D-phenylalanine
• 英文别名: D-4-aminophenylalanine；4-amino-D-phenylalanine；4-Amino-D-phenylalanin；4-amino-L-phenylalanine；(2R)-3-(4-aminophenyl)-2-azaniumyl-propanoate；(2R)-3-(4-aminophenyl)-2-azaniumylpropanoate
• CAS: 102281-45-8
• 化学式: C₉H₁₂N₂O₂
• mdl: MFCD00069926
• 分子量: 180.206
• InChiKey: CMUHFUGDYMFHEI-MRVPVSSYSA-N

物化性质

• 熔点：
  268-270 °C(lit.)
• 沸点：
  383.5±32.0 °C(Predicted)
• 密度：
  1.289±0.06 g/cm3(Predicted)
• 溶解度：
  H2O：20 mg/mL，可溶

计算性质

• 辛醇/水分配系数(LogP)：
  -2.2
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  89.3
• 氢给体数：
  3
• 氢受体数：
  4

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S36
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  对氨基-DL-苯丙氨酸水合物	(p-aminophenyl)alanine	2922-41-0	C9H12N2O2	180.206
  4-硝基-L-苯丙氨酸	4-nitro-3-phenyl-L-alanine	949-99-5	C9H10N2O4	210.189

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	4-amino L-phenylalanine ethyl ester	126257-08-7	C11H16N2O2	208.26
  ——	4-amino-3-chloro-D-phenylalanine	240428-46-0	C9H11ClN2O2	214.652

反应信息

• 作为反应物：
  描述：

  4-氨基-D-苯丙氨酸 在 N-甲基吗啉 、 sodium hydroxide 、 氯化亚砜 、 氢溴酸 、 溴 、 溶剂黄146 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 为溶剂， 反应 7.75h， 生成 N²-[4-amino-3,5-dibromo-N-(3-phenyl-1-oxopropyl)-D-phenylalanyl]-N⁶-(phenylmethoxycarbonyl)-L-lysine-2-phenethylamide
  参考文献：
  名称：

  Development of Human Calcitonin Gene-Related Peptide (CGRP) Receptor Antagonists. 1. Potent and Selective Small Molecule CGRP Antagonists. 1-[N²-[3,5-Dibromo-N-[[4-(3,4-dihydro-2(1H)-oxoquinazolin-3-yl)-1- piperidinyl]carbonyl]-d-tyrosyl]-l-lysyl]-4-(4-pyridinyl)piperazine:  The First CGRP Antagonist for Clinical Trials in Acute Migraine

  摘要：

  Although the triptans have greatly improved the acute treatment of migraine headache, there are yet many shortcomings. Therefore, new strategies for the treatment of migraine are needed which offer advantages over current therapy, e.g. triptans. Our novel approach was based on the hypothesis that the release of calcitonin gene-related peptide (CGRP) could play a causative role in migraine headache. Thus we initiated a program aimed at the design and synthesis of small molecule CGRP receptor antagonists. High throughput screening led to the identification of (R)-Tyr-(S)-Lys dipeptide-like compounds that showed weak but unequivocal binding to the human CGRP receptor. Lead optimization afforded highly potent CGRP antagonists, the prototype being compound 19 (BIBN4096). This compound exhibiting a favorable biological profile was selected for initial clinical trials. A proof of concept study indicated that intravenous application of 19 was effective in the treatment of acute migraine headache. This finding strongly supports our initial working hypothesis that CGRP plays an important role in the pathophysiology of migraine.

  DOI：

  10.1021/jm0490641
• 作为产物：
  描述：

  4-amino-α-benzoylamino-trans-cinnamic acid-((1R)-menthyl ester) 在 aluminum oxide 、 palladium/alumina 、 乙酸乙酯 作用下， 生成 4-氨基-D-苯丙氨酸
  参考文献：
  名称：

  对取代苯丙氨酸衍生物的部分不对称合成

  摘要：

  描述了α-苯甲酰基氨基-对硝基肉桂酸的乙酯，薄荷基和冰片酯的代表及其还原为相应的χ-苯甲酰基氨基-对氨基肉桂酸的酯。

  DOI：

  10.1002/hlca.19570400108

文献信息

• [EN] AZASULFURYLPEPTIDE-BASED CD36 MODULATORS AND USES THEREOF<br/>[FR] MODULATEURS CD36 À BASE D'AZASULFURYLPEPTIDES ET UTILISATIONS DE CEUX-CI
  申请人：RSEM LTD PARTNERSHIP

  公开号：WO2016029324A1

  公开（公告）日：2016-03-03

  Novel azasulfuryl-containing peptidomimetics capable of inhibiting CD36 activity are disclosed. Use of these azasulfuryl-containing peptidomimetics for the treatment of CD36-related diseases, disorders or conditions, including TLR2-mediated inflammatory disease, disorder or condition, and methods of obtaining such azasulfuryl-containing peptidomimetics, are also disclosed.

  揭示了能够抑制CD36活性的新型含氮硫酰基的肽类模拟物。还揭示了利用这些含氮硫酰基的肽类模拟物治疗与CD36相关的疾病、紊乱或状况，包括TLR2介导的炎症性疾病、紊乱或状况的用途，以及获取这种含氮硫酰基的肽类模拟物的方法。
• [EN] PSMA LIGANDS FOR IMAGING AND ENDORADIOTHERAPY<br/>[FR] LIGANDS DE PSMA POUR L'IMAGERIE ET L'ENDORADIOTHÉRAPIE
  申请人：UNIV MUENCHEN TECH

  公开号：WO2019115547A1

  公开（公告）日：2019-06-20

  The present disclosure relates to imaging and endoradiotherapy of diseases involving prostate-specific membrane antigen (PSMA). Provided are compounds which bind or inhibit PSMA and furthermore carry at least one moiety which is amenable to radiolabeling. Provided are also medical uses of such compounds.

  本公开涉及涉及前列腺特异性膜抗原（PSMA）相关疾病的成像和内放射治疗。提供了结合或抑制PSMA并且携带至少一个适合于放射标记的基团的化合物。还提供了这类化合物的医疗用途。
• Lipid probes and uses thereof
  申请人：THE SCRIPPS RESEARCH INSTITUTE

  公开号：US10168342B2

  公开（公告）日：2019-01-01

  Disclosed herein are methods, compositions, probes, assays and kits for identifying a lipid binding protein as a drug binding target. Also disclosed herein are methods, compositions, and probes for mapping a ligand binding site on a lipid binding protein, identification of lipid binding proteins, generating drug-lipid binding protein profiles, high throughput drug screening, and identification of drugs as potential lipid binding protein ligands.

  披露了用于识别脂质结合蛋白作为药物结合靶点的方法、组合物、探针、检测和试剂盒。此外，还披露了用于绘制脂质结合蛋白上的配体结合位点、识别脂质结合蛋白、生成药物-脂质结合蛋白轮廓、高通量药物筛选以及识别作为潜在脂质结合蛋白配体的药物的方法、组合物和探针。
• [EN] POLYMERIC HYPERBRANCHED CARRIER-LINKED PRODRUGS<br/>[FR] PROMÉDICAMENTS LIÉS À DES EXCIPIENTS POLYMÉRIQUES HYPERBRANCHÉS
  申请人：ASCENDIS PHARMA AS

  公开号：WO2013024048A1

  公开（公告）日：2013-02-21

  The present invention relates to water-soluble carrier-linked prodrugs of formula (I),wherein POL is a polymeric moiety,each Hyp is independently a hyperbranched moiety,each moiety SP is independently a spacer moiety, each L is independently a reversible prodrug linker moiety, m is 0 or 1, each n is independently an integer from 2 to 200 and each x is independently 0 or 1. It further relates to pharmaceutical compositions comprising said water- soluble carrier-linked prodrugs and methods of treatment.

  本发明涉及水溶性载体连接的前药，其化学式为（I），其中POL是聚合物基团，每个Hyp是独立的超支化基团，每个基团SP是独立的间隔基团，每个L是独立的可逆前药连接基团，m为0或1，每个n是独立的整数，范围从2到200，每个x是独立的0或1。此外，还涉及包含所述水溶性载体连接的前药的药物组合物和治疗方法。
• CONFORMATIONALLY CONSTRAINED, FULLY SYNTHETIC MACROCYCLIC COMPOUNDS
  申请人：Obrecht Daniel

  公开号：US20120202821A1

  公开（公告）日：2012-08-09

  Conformationally restricted, spatially defined 12-30 membered macrocyclic ring systems of type (I) are constituted by three distinct building blocks: an aromatic template a, a conformation modulator b and a spacer moiety c as detailed in the description and the claims. Macrocycles of type (I) are readily manufactured by parallel synthesis or combinatorial chemistry. They are designed to interact with specific biological targets. In particular, they show agonistic or antagonistic activity on the motilin receptor (MR receptor), on the serotonin receptor of subtype 5-HT 2B (5-HT 2B receptor), and on the prostaglandin F2•receptor (FP receptor). They are thus potentially useful for the treatment of hypomotility disorders of the gastrointestinal tract such as diabetic gastroparesis and constipation type irritable bowl syndrome; of CNS related diseases like migraine, schizophrenia, psychosis or depression; of ocular hypertension such as associated with glaucoma and preterm labour.

  构象受限、空间定义的12-30环大环环系统(I型)由三个不同的构建模块组成：芳香模板a、构象调节剂b和间隔基团c，如详细描述和索赔中所述。类型(I)的大环可通过并行合成或组合化学方法轻松制备。它们被设计用于与特定生物靶点相互作用。特别是，它们在胃动素受体(MR受体)、5-HT2B亚型的5-羟色胺受体(5-HT2B受体)和前列腺素F2受体(FP受体)上显示出激动或拮抗活性。因此，它们潜在地可用于治疗胃肠道低动力障碍，如糖尿病性胃轻瘫和便秘型肠易激综合征；中枢神经系统相关疾病，如偏头痛、精神分裂症、精神病或抑郁症；眼压增高，如青光眼和早产。