6-硝基-D-色氨酸 | 56937-50-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 中文名称: 6-硝基-D-色氨酸
• 英文名称: 6-nitro-D-tryptophan
• 英文别名: (2R)-2-amino-3-(6-nitro-1H-indol-3-yl)propanoic acid
• CAS: 56937-50-9
• 化学式: C₁₁H₁₁N₃O₄
• 分子量: 249.226
• InChiKey: AWLWPSSHYJQPCH-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  125
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-硝基-D-色氨酸 在 氯化亚砜 、 水 、 四丁基硫酸氢铵 、 4-甲基苯磺酸吡啶 、 potassium carbonate 、 sodium sulfate 、 间氯过氧苯甲酸 、 sodium hydroxide 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 10.0h， 生成 1,8-bis(tert-butoxycarbonyl)-3a-hydroxy-6-nitro-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole-2-carboxylic acid
  参考文献：
  名称：

  [EN] A CONJUGATE OF AN AMANITA TOXIN WITH BRANCHED LINKERS
  [FR] CONJUGUÉ D'UNE TOXINE D'AMANITE AVEC DES LIEURS RAMIFIÉS

  摘要：

  本文提供了一种将鹅膏菌毒素化合物与具有分支连接物的细胞结合分子结合，以实现更好地针对异常细胞进行治疗。它还涉及将鹅膏菌分子与细胞结合配体结合的分支连接方法，以及在癌症、感染和自身免疫疾病治疗中使用该结合物的方法。

  公开号：

  WO2020155017A1
• 作为产物：
  描述：

  2-碘-5-硝基苯胺 在 palladium diacetate 盐酸 、 sodium hydroxide 、 四丁基氟化铵 、 sodium carbonate 、 lithium chloride 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 6-硝基-D-色氨酸
  参考文献：
  名称：

  光学活性环A取代色氨酸作为IDO抑制剂的合成

  摘要：

  描述了光学活性的7-甲氧基-d-色氨酸以及其他被A环取代的色氨酸的第一合成。

  DOI：

  10.1016/j.tetlet.2004.09.113

文献信息

• The facile synthesis of a series of tryptophan derivatives
  作者：Georg Blaser、John M. Sanderson、Andrei S. Batsanov、Judith A.K. Howard

  DOI：10.1016/j.tetlet.2008.02.120

  日期：2008.4

  of 5- and 6-substituted tryptophan derivatives that are difficult to prepare using alternative enzymatic approaches. Acylation of an activated amino acid, derived from serine in situ, is coupled with an enzymatic resolution step to furnish enantiopure analogues bearing a range of electron withdrawing and releasing substituents. Isolation of a dehydroalanine derivative as a by-product from some reactions

  这项研究报告了一种简便的方法，用于合成各种5和6取代的色氨酸衍生物，这些色素很难使用替代酶方法制备。原位衍生自丝氨酸的活化氨基酸的酰化与酶促拆分步骤相结合，以提供带有一系列吸电​​子和释放电子的取代基的对映纯类似物。从某些反应中分离出作为副产物的脱氢丙氨酸衍生物，可为该反应的可能机理提供一些见解。
• Antigen-presenting cell populations and their use as reagents for enhancing or reducing immune tolerance
  申请人：Medical College of Georgia Research Institute, Inc

  公开号：EP2177601A1

  公开（公告）日：2010-04-21

  The present invention is based on the discovery antigen-presenting cells (APCs) may be generated to have predetermined levels of expression of the intracellular enzyme, indoleamine 2,3-dioxygenase (IDO). Because expression of high levels of IDO is correlated with a reduced ability to stimulate T cell responses and an enhanced ability to induce immunologic tolerance, APCs having high levels of IDO may be used to increase tolerance in the immune system, as for example in transplant therapy or treatment of autoimmune disorders. For example, APCs having high levels of IDO, and expressing or loaded with at least one antigen from a donor tissue may be used to increase tolerance of the recipient to the donor's tissue. Alternatively, APCs having reduced levels of IDO expression and expressing or loaded with at least one antigen from a cancer or infectious pathogen may be used as vaccines to promote T cell responses and increase immunity.

  本发明的基础是发现抗原递呈细胞（APCs）可以生成具有预定表达水平的细胞内酶--吲哚胺 2,3-二氧化酶（IDO）。由于高水平 IDO 的表达与刺激 T 细胞反应的能力降低和诱导免疫耐受的能力增强相关，因此具有高水平 IDO 的 APCs 可用来增加免疫系统的耐受性，例如在移植疗法或自身免疫性疾病的治疗中。例如，具有高水平 IDO 并表达或负载至少一种供体组织抗原的 APCs 可用于提高受体对供体组织的耐受性。另外，IDO 表达水平降低、表达或负载至少一种癌症或传染性病原体抗原的 APCs 可用作疫苗，以促进 T 细胞反应并增强免疫力。
• Use of inhibitors of indoleamine-2,3-dioxygenase in combination with other therapeutic modalities
  申请人：Medical College of Georgia Research Institute, Inc.

  公开号：US20040234623A1

  公开（公告）日：2004-11-25

  The present invention provides improved treatment methods by the administration of both an inhibitor of indoleamine-2,3-dioxygenase in addition to the administration of an additional therapeutic agent.

  本发明通过同时使用吲哚胺-2,3-二氧 化酶抑制剂和额外的治疗药物，提供了改进的治疗方法。
• New effective gonadotropin releasing hormone antagonists with minimal potency for histamine release in vitro
  作者：Jean E. Rivier、John Porter、Catherine L. Rivier、Marilyn Perrin、Anne Corrigan、William A. Hook、Reuben P. Siraganian、Wylie W. Vale

  DOI：10.1021/jm00160a008

  日期：1986.10

  In order to minimize the adverse effect of histamine release in the rat of some gonadotropin releasing hormone (GnRH) antagonists, such as [Ac-D2Nal1,D4FPhe2,DTrp3,DArg6]-GnRH, new structures with modifications at positions 1, 2, 3, 5, 6, 7, and 10 were synthesized and tested in several biological systems. In vitro: the affinity for the pituitary GnRH receptor was measured as was the ability of the analogues to inhibit GnRH-stimulated release of luteinizing hormone (LH) by dispersed anterior pituitary cells in culture and to release histamine from rat mast cells. In vivo: inhibition of ovulation in the cycling rat was determined after subcutaneous (sc) injection of the peptides at noon on the day of proestrus; the duration of action of the peptides was evaluated by measuring LH levels in the castrated male rat after sc injection of some selected analogues. [Ac-D2Nal1,D4ClPhe2,D3Pal3,Arg5,D-4-p-methoxy benzoyl-2-aminobutyric acid6,DAla10]-GnRH was found to be one of the most potent analogues of this series, causing a 100% inhibition of ovulation at 5 micrograms/kg or less. Release of histamine was observed at doses 10-25 times that required for [Ac-D2Nal1,D4FPhe2,DTrp3,DArg6]-GnRH. Thus, introduction of arginine in position 5 with a hydrophobic amino acid in position 6 is compatible with high potency in several biological systems and results in compounds with lowered potency to release histamine compared to homologous peptides with tyrosine in position 5 and D-arginine in position 6.
• Somatostatin-analoge Cyclopeptide, Verfahren zu ihrer Herstellung, pharmazeutische Präparate enthaltend diese Verbindungen, sowie ihre therapeutische Anwendung
  申请人：CIBA-GEIGY AG

  公开号：EP0001295B1

  公开（公告）日：1982-03-17