N_b-carbomethoxyindole-3-methanamine

• 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
• 英文名称: N_b-carbomethoxyindole-3-methanamine
• 英文别名: methyl N'-(3-indolylmethyl)carbamate；methyl N-(indol-3-ylmethyl)carbamate；methyl N-(3-indolylmethyl)carbamate；methyl N-(1H-indol-3-ylmethyl)carbamate
• 化学式: C₁₁H₁₂N₂O₂
• 分子量: 204.228
• InChiKey: VSKMGYWLFHMVGB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 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：
  54.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N_b-carbomethoxyindole-3-methanamine 在 L-1,4-二硫代苏糖醇 、 Leptosphaeria maculans brassinin oxidase 、 水 、 5-甲基吩嗪硫酸甲酯 、 二乙醇胺 作用下， 生成 3-吲哚甲醛
  参考文献：
  名称：

  Brassinin oxidase mediated transformation of the phytoalexin brassinin: Structure of the elusive co-product, deuterium isotope effect and stereoselectivity

  摘要：

  Brassinin oxidase, a fungal detoxifying enzyme that mediates the conversion of the phytoalexin brassinin into indole-3-carboxaldehyde, is the first enzyme described to date that catalyzes the transformation of a dithiocarbamate group into an aldehyde equivalent. Brassinin is an essential phytoalexin due to its antifungal activity and its role as biosynthetic precursor of other phytoalexins produced in plants of the family Brassicaceae (common name crucifer). In this report, the isolation, structure determination and synthesis of the elusive co-product of brassinin transformation by brassinin oxidase, S-methyl dithiocarbamate, the syntheses of dideuterated and (R) and (S) monodeuterated brassinins, kinetic analyses of isotope effects and chemical modifications of brassinin oxidase are described. The reaction of [1'-H-2(2)] brassinin was found to be slowed by a kinetic isotope effect of 5.3 on the value of k(cat)/K-m. This result indicates that the hydride/hydrogen transfer step preceding brassinin transformation is rate determining in the overall reaction. In addition, the use of (R) and (S)-[1'-H-2] brassinins as substrates indicated that the hydride/hydrogen transfer step is ca. 88% stereoselective for the pro-R hydrogen. A detailed chemical mechanism of the enzymatic transformation of brassinin is proposed. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.01.011
• 作为产物：
  描述：

  吲哚-3-甲胺 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 N_b-carbomethoxyindole-3-methanamine
  参考文献：
  名称：

  植物病原真菌对植物抗毒素芸苔素类似物的代谢

  摘要：

  十字花科植物抗毒素芸苔素类似物由植物病原真菌 Phoma lingam (Tode ex Fr.)“有毒”和“无毒”组（有性阶段 Leptosphaeria maculans (Desm.) Ces. et de Not.）和 Alternaria brassicae (Berk) 代谢.) 囊。被报道。已确定每种病原体都能解毒甲基色胺二硫代氨基甲酸酯，尽管产生不同的代谢产物。虽然毒性 P. lingam 的生物转化继续产生甲基 3a-羟基-3,3a,8,8a-四氢吡咯并[2,3-b]indol-1(2H)-yl carbodithioate 和 indole-3-乙酸作为最终产物产品中，无毒的 P. lingam 通过 Nb-乙酰色胺产生吲哚-3-羧酸，而芸苔属植物产生 Nb-乙酰色胺，作为最终产品。此外，为了确定二硫代氨基甲酸酯基团在对抗 P. lingam 和 A. brasicae

  DOI：

  10.1139/v00-024

文献信息

• Preparation of Alkyl Carbamate of 1‐Protected Indole‐3‐methylamine as a Precursor of Indole‐3‐methylamine
  作者：Hao Song、Wei Chen、Yin Wang,、Yong Qin

  DOI：10.1080/00397910500287967

  日期：2005.11.1

  Abstract A series of alkyl carbamates 3 of 1‐protected indole‐3‐methylamines, alkyl carbamates 6 of thiophenylmethylamines, and pyrrolylmethylamines were prepared from the corresponding acetamides 2 and 5 in good to excellent yields via diacetoxyiodobenzene‐promoted Hofmann rearrangement. For a successful Hofmann rearrangement, an electron‐withdrawing group on position 1 of indolylacetamide and pyrrolylacetamide

  摘要 通过二乙酰氧基碘苯促进的霍夫曼重排，以相应的乙酰胺 2 和 5 为原料制备了一系列 1-保护的吲哚-3-甲胺的氨基甲酸烷基酯 3、苯硫基甲胺的氨基甲酸烷基酯 6 和吡咯基甲胺。为了成功进行霍夫曼重排，需要在吲哚乙酰胺和吡咯乙酰胺的 1 位上有一个吸电子基团。氨基甲酸烷基酯 3g 被证明可以很好地作为 1-保护的吲哚-3-甲胺 1 的稳定前体。
• [EN] FUSED THIAZOLE AND THIOPHENE DERIVATIVES AS KINASE INHIBITORS<br/>[FR] DÉRIVÉS THIAZOLE ET THIOPHÈNE FUSIONNÉS COMME INHIBITEURS DE KINASE
  申请人：UCB PHARMA SA

  公开号：WO2009071895A1

  公开（公告）日：2009-06-11

  A series of fused bicyclic thiazole and thiophene derivatives which are substituted in the 2-position by an optionally substituted morpholin-4-yl moiety, and in the 4-position by hydroxy, oxo or an amine moiety, being selective inhibitors of PI3 kinase enzymes, are accordingly of benefit in medicine, for example in the treatment of inflammatory, autoimmune, cardiovascular, neurodegenerative, metabolic, oncological, nociceptive or ophthalmic conditions. (I)

  一系列在2位被一个可选择取代的吗啡啉-4-基团取代，并在4位被羟基、酮基或胺基团取代的融合双环噻唑和噻吩衍生物，作为选择性PI3激酶酶抑制剂，在医学上具有益处，例如在治疗炎症、自身免疫、心血管、神经退行性、代谢、肿瘤、疼痛或眼科疾病方面。（I）
• [EN] TRICYCLIC KINASE INHIBITORS<br/>[FR] INHIBITEURS TRICYCLIQUES DE KINASE
  申请人：UCB PHARMA SA

  公开号：WO2009071890A1

  公开（公告）日：2009-06-11

  A series of fused tricyclic thiazole and thiophene derivatives which are substituted in the 2-position of the thiazole or thiophene ring by an optionally substituted morpholin-4-yl moiety, being selective inhibitors of PI3 kinase enzymes, are accordingly of benefit in medicine, for example in the treatment of inflammatory, autoimmune, cardiovascular, neurodegenerative, metabolic, oncological, nociceptive or ophthalmic conditions.

  一系列融合的三环噻唑和噻吩衍生物，其在噻唑或噻吩环的2位被一个可选择取代的吗啡啉-4-基团取代，是选择性PI3激酶酶抑制剂，在医学上具有益处，例如在治疗炎症性、自身免疫性、心血管、神经退行性、代谢性、肿瘤学、疼痛性或眼科疾病方面。
• Toward the control of Leptosphaeria maculans: Design, syntheses, biological activity, and metabolism of potential detoxification inhibitors of the crucifer phytoalexin brassinin
  作者：M. Soledade C. Pedras、Mukund Jha

  DOI：10.1016/j.bmc.2006.03.014

  日期：2006.7.15

  with the potential inhibitors and brassinin: (1) a decrease on the rate of brassinin detoxification due to the strong inhibitory activity of the compound on fungal growth, (2) a decrease on the rate of brassinin detoxification due to the inhibitory activity of the compound on the putative brassinin oxidase, and (3) a low to no detectable effect on the rate of brassinin detoxification. A noticeable decrease

  十字花科植物（1）是十字花科植物产生的至关重要的植物防御作用，它是利用植物病原真菌Leptosphaeria maculans（Phoma lingam）使用推定的黄铜花系氧化酶将其解毒为吲哚3-甲醛。通过用氨基甲酸酯，二硫代碳酸盐，尿素，硫脲，磺酰胺，磺酰胺，二硫代氨基甲酸酯，酰胺和酯官能团代替其二硫代氨基甲酸酯基团（毒素），设计出了油菜青素解毒的潜在抑制剂。另外，吲哚基部分被萘基和苯基取代。据报道，这些潜在的排毒抑制剂的合成和化学表征，以及它们的抗真菌和细胞毒性活性，以及​​使用黄斑狼疮菌培养物进行筛选。总的来说，在L的培养物中观察到三种类型的相互作用。与潜在抑制剂和油菜素共孵育的黄斑：（1）由于该化合物对真菌生长的抑制作用强，因此油菜素的解毒率降低；（2）由于抑制作用，油菜素的解毒率降低化合物对假定的油菜蛋白氧化酶的活性；以及（3）对油菜蛋白的解毒速率影响很小甚至没有可检测的作用。在
• [EN] PYRROLOTHIAZOLES AS PI3-KINASE INHIBITORS<br/>[FR] PYRROLOTHIAZOLES COMME INHIBITEURS DE LA PI3 KINASE
  申请人：UCB PHARMA SA

  公开号：WO2009071888A1

  公开（公告）日：2009-06-11

  A series of 4,5-dihydro-6H-pyrrolo[3,4-d][1,3]thiazol-6-one derivatives, and analogues thereof, which are substituted in the 2-position by an optionally substituted morpholin-4-yl moiety, being selective inhibitors of PI3 kinase enzymes, are accordingly of benefit in medicine, for example in the treatment of inflammatory, autoimmune, cardiovascular, neurodegenerative, metabolic, oncological, nociceptive or ophthalmic conditions.

  一系列在2-位置被一个可选择取代的吗啡啶-4-基团取代的4,5-二氢-6H-吡咯并[3,4-d][1,3]噻唑-6-酮衍生物及其类似物，是选择性PI3激酶酶抑制剂，在医学上具有益处，例如在治疗炎症、自身免疫、心血管、神经退行性、代谢、肿瘤、疼痛或眼科疾病方面。