N-1-(tert-butoxycarbonyl)-N-2-(cyclohexylmethyl)hydrazine | 149267-56-1

• 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
• 英文名称: N-1-(tert-butoxycarbonyl)-N-2-(cyclohexylmethyl)hydrazine
• 英文别名: 1-(cyclohexylmethyl)-2-Boc-hydrazine；N1-Boc-N2-cyclohexyl-hydrazine；tert-butyl-3-cyclohexylmethyl-carbazate；Hydrazinecarboxylic acid, 2-(cyclohexylmethyl)-, 1,1-dimethylethyl ester；tert-butyl N-(cyclohexylmethylamino)carbamate
• CAS: 149267-56-1
• 化学式: C₁₂H₂₄N₂O₂
• 分子量: 228.335
• InChiKey: ONWQGXWSSLUZOC-UHFFFAOYSA-N

物化性质

• 密度：
  0.987±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  50.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-1-(tert-butoxycarbonyl)-N-2-(cyclohexylmethyl)hydrazine 在 N-甲基吗啉 、 甲酸 、 potassium carbonate 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 3-羟基-1,2,3-苯并三嗪-4(3H)-酮 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 乙腈 为溶剂， 反应 114.0h， 生成 (2S)-N-[(2S,3S)-4-[[[(2S)-2-amino-3-methylbutanoyl]amino]-(cyclohexylmethyl)amino]-3-hydroxy-1-phenylbutan-2-yl]-2-(quinoline-2-carbonylamino)butanediamide
  参考文献：
  名称：

  Aza-Peptide Analogs as Potent Human Immunodeficiency Virus Type-1 Protease Inhibitors with Oral Bioavailability

  摘要：

  A series of aza-peptide analogs with a (hydroxyethyl)hydrazine isostere has been synthesized as HIV-1 protease inhibitors using a simple synthetic scheme. Structure-activity studies based on the X-ray of a previously described inhibitor-enzyme complex led to potent inhibitors with antiviral activity in the low-nanomolar range. The S-configuration of the transition-state hydroxyl group was preferred in this series. Small modifications of the P2P3 and P-2'P-3' substituents had little effect on enzyme inhibition but greatly influenced the pharmacokinetic profile. As a result of these studies, the symmetrically acylated compound 8a and its close analog 24a bearing a methyl carbamate in P-3 and an ethyl carbamate in P-3' position were identified as potent inhibitors with plasma concentrations exceeding antiviral ED(50) values 150-fold following oral application in mice.

  DOI：

  10.1021/jm960022p
• 作为产物：
  描述：

  肼基甲酸叔丁酯 在 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 生成 N-1-(tert-butoxycarbonyl)-N-2-(cyclohexylmethyl)hydrazine
  参考文献：
  名称：

  一系列新型的，含一氧化氮供体的吡唑类化合物的合成和选择性的环氧合酶-2抑制活性。

  摘要：

  据报道一系列含有硝酸盐（ONO（2））作为一氧化氮（NO）-供体官能团的新型吡唑的合成。分析了它们在人全血中对COX-1和COX-2的抑制活性。我们的数据表明，吡唑环取代基在COX-2选择性抑制中起重要作用，因此发现环烷基吡唑（6b）是一种有效且选择性的COX-2抑制剂。在中心吡唑环（17b，23b，26b-1）的3位上的其他修饰增强了COX-2抑制能力。在合成的吡唑中，肟（23b）被确定为最有效的COX-2选择性抑制剂。因此，口服给药后在大鼠中进行了药理学分析，结果表明23b在角叉菜胶诱导的气袋模型中具有有效的抗炎活性，并且与背景阿司匹林一起给药时，胃毒性比标准COX-2抑制剂低。我们建议，NO供体COX-2选择性抑制剂的胃耐受性增强，有可能增加该药物类别的临床表现。

  DOI：

  10.1021/jm030276s

文献信息

• Falcipain Inhibitors: Optimization Studies of the 2-Pyrimidinecarbonitrile Lead Series
  作者：Jose M. Coterón、David Catterick、Julia Castro、María J. Chaparro、Beatriz Díaz、Esther Fernández、Santiago Ferrer、Francisco J. Gamo、Mariola Gordo、Jiri Gut、Laura de las Heras、Jennifer Legac、Maria Marco、Juan Miguel、Vicente Muñoz、Esther Porras、Juan C. de la Rosa、Jose R. Ruiz、Elena Sandoval、Pilar Ventosa、Philip J. Rosenthal、Jose M. Fiandor

  DOI：10.1021/jm100556b

  日期：2010.8.26

  were studied as potential falcipain inhibitors and therefore potential antiparasitic lead compounds, with the 5-substituted-2-cyanopyrimidine chemical class emerging as the most potent and promising lead series. Through a sequential lead optimization process considering the different positions present in the initial scaffold, nanomolar and subnanomolar inhibitors at falcipains 2 and 3 were identified

  Falcipain-2和falcipain-3是疟原虫恶性疟原虫的木瓜蛋白酶家族半胱氨酸蛋白酶负责宿主血红蛋白水解以提供用于寄生虫蛋白质合成的氨基酸。研究了不同的杂芳基腈衍生物作为潜在的falcipain抑制剂，因此潜在的抗寄生虫铅化合物，其中5-取代的2-氰基嘧啶化学类别成为最有效和有前途的铅系列。考虑到初始支架中存在的不同位置，通过顺序的前导优化过程，鉴定出了在恶性激素2和3处的纳摩尔和亚纳摩尔抑制剂，并具有在微摩尔范围内对抗培养的寄生虫的活性。在铅分子中引入质子化胺后，对培养的寄生虫的活性显着提高了1000倍，而其他SAR趋势没有明显改变。
• Antiretroviral hydrazine derivatives
  申请人：Novartis Corporation

  公开号：US05753652A1

  公开（公告）日：1998-05-19

  The invention relates to compounds of formula ##STR1## and salts, pharmaceutical compositions, intermediates and processes of preparation thereof.

  本发明涉及具有公式##STR1##的化合物及其盐、药物组合物、中间体及其制备方法。
• PYRAZOLE COMPOUND
  申请人：Sasaki Izumi

  公开号：US20130116296A1

  公开（公告）日：2013-05-09

  The present invention relates to a novel serotonin reuptake inhibitor which also exhibits 5-HT 2C antagonistic action (antidepressive and anxiolytic effects), in particular, 5-HT 2C inverse agonistic action comprising Compound (1): or a pharmaceutically acceptable salt thereof wherein R 1 , R 2 , R 3 and R 4 are independently hydrogen or C 1-6 alkyl etc.; R 5 is C 4-7 alkyl or —(CR 8 R 9 ) r -E; R 6 , R 7 , R 8 and R 9 are independently hydrogen, fluorine or C 1-6 alkyl; A is C 6-10 aryl or heteroaryl etc.; r is 1, 2, 3 or 4; E is C 3-8 cycloalkyl or C 6-10 aryl etc.; L is oxygen, sulfur or —NR 10 —; n is 1, 2 or 3; R 10 is hydrogen or C 1-6 alkyl etc.; and X is hydrogen or halogen etc.

  本发明涉及一种新型的血清素再摄取抑制剂，同时还表现出5-HT2C拮抗作用（抗抑郁和抗焦虑效果），特别是包括化合物（1）的5-HT2C逆作动作：或其药学上可接受的盐，其中R1、R2、R3和R4独立地为氢或C1-6烷基等；R5为C4-7烷基或—(CR8R9)r-E；R6、R7、R8和R9独立地为氢、氟或C1-6烷基；A为C6-10芳基或杂环芳基等；r为1、2、3或4；E为C3-8环烷基或C6-10芳基等；L为氧、硫或—NR10—；n为1、2或3；R10为氢或C1-6烷基等；X为氢或卤素等。
• One-Pot Synthesis of New Fused 4,5-Bridged 1,2,5-Triazepine-3,6-diones, 1,2,5-Triazepine-3,7-diones Heterocycles by Petasis Reaction
  作者：Subhasish Neogi、Amrita Roy、Dinabandhu Naskar

  DOI：10.1021/cc900092x

  日期：2010.1.11

  The one pot synthesis of a new fused 1,2,5-triazepine-3,6-diones, 1,2,5-triazepine-3,7-diones heterocyles has been described via Petasis reactions. These heterocycles might be suitable for elaboration into larger peptides at amino termini. The scope and limitations of this method have been examined.

  已经通过Petasis反应描述了新的稠合的1,2,5-三氮杂3,6-二酮，1,2,5-三氮杂-3,7-二酮杂环的一锅合成。这些杂环可能适合在氨基末端加工成更大的肽。已经检查了该方法的范围和局限性。
• Synthesis and Properties of Hydrazino Amino Acyclic Carbenes of Gold(I), Platinum(II), Palladium(II) and Rhodium(III)
  作者：Svetlana Tšupova、Matthias Rudolph、Frank Rominger、A. Stephen K. Hashmi

  DOI：10.1002/adsc.201600615

  日期：2016.12.22

  The nucleophilic addition of protected and substituted hydrazine derivatives to isonitrile complexes of gold(I), platinum(II), palladium(II) and rhodium(III) provides the corresponding hydrazino amino acyclic carbene complexes. These are characterized by their spectroscopic data, four different X‐ray single crystal structure analyses and their catalytic activity in the gold(I)‐catalyzed cycloisomerization

  将受保护和取代的肼衍生物亲核加成到金（I），铂（II），钯（II）和铑（III）的异腈配合物中，提供了相应的肼基氨基无环卡宾配合物。它们的特征在于其光谱数据，四种不同的X射线单晶结构分析及其在金（I）催化的N-炔丙基甲酰胺向亚烷基新恶唑啉的环异构化中的催化活性。