4-nitro-1-H-pyrazole-1-carboxamidine | 187022-33-9

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 4-nitro-1-H-pyrazole-1-carboxamidine
• 英文别名: 2-nitropyrazole-1-N,N'-bis(tert-butoxycarbonyl)carboxamidine；4-nitro-N,N'-di-boc-1h-pyrazole-1-carboxamidine；tert-butyl N-[[(2-methylpropan-2-yl)oxycarbonylamino]-(4-nitropyrazol-1-yl)methylidene]carbamate
• CAS: 187022-33-9
• 化学式: C₁₄H₂₁N₅O₆
• 分子量: 355.351
• InChiKey: JXXBQIMISRTYOY-UHFFFAOYSA-N

物化性质

• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  141
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  苄胺 、 4-nitro-1-H-pyrazole-1-carboxamidine 以 N,N-二甲基甲酰胺 为溶剂， 以94%的产率得到N,N''-bis(tert-butoxycarbonyl)-N'-(benzyl)guanidine
  参考文献：
  名称：

  从胺固相和液相合成受保护的胍的新试剂

  摘要：

  已开发出一种新的试剂4-硝基-1- H-吡唑-1- [ N，N'-双（叔丁氧基羰基）]car☐idine-可快速有效地合成双（氨基甲酸酯）伯胺和仲胺保护的胍。该试剂是文献试剂1 - H-吡唑-1- [ N，N'-双（叔丁氧羰基）]car☐☐的亲电子性更高的反应性衍生物。新试剂的反应性提高，使其溶液产率提高，并且在对与树脂结合的胺进行胍基化时需要更少的当量。

  DOI：

  10.1016/s0040-4039(98)80017-8
• 作为产物：
  描述：

  4-硝基吡唑 、 N,N′-二-Boc-硫脲 在 三乙胺 、 mercury dichloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以59%的产率得到4-nitro-1-H-pyrazole-1-carboxamidine
  参考文献：
  名称：

  从胺固相和液相合成受保护的胍的新试剂

  摘要：

  已开发出一种新的试剂4-硝基-1- H-吡唑-1- [ N，N'-双（叔丁氧基羰基）]car☐idine-可快速有效地合成双（氨基甲酸酯）伯胺和仲胺保护的胍。该试剂是文献试剂1 - H-吡唑-1- [ N，N'-双（叔丁氧羰基）]car☐☐的亲电子性更高的反应性衍生物。新试剂的反应性提高，使其溶液产率提高，并且在对与树脂结合的胺进行胍基化时需要更少的当量。

  DOI：

  10.1016/s0040-4039(98)80017-8

文献信息

• Dendrimers as molecular translocators
  申请人：Goodman Murray

  公开号：US20060216265A1

  公开（公告）日：2006-09-28

  Transport molecules include a dendrimer and a biologically active molecule. The dendrimer of such transport molecules includes at least one guanidine group, at least one protonated guanidine group, at least one protected guanidine group, at least one amidine group, at least one protonated amidine group, at least one protected amidine group, at least one ureido group, at least one protonated ureido group, at least one protected ureido group, at least one thioureido group, at least one protonated thioureido group, or at least one protected thioureido group. The biologically active molecule is bonded to the dendrimer. A method of increasing the bioavailability of a drug includes bonding the drug to a dendrimer of the invention.

  转运分子包括一种树枝状聚合物和一种生物活性分子。这些转运分子的树枝状聚合物包括至少一个胍基团、至少一个质子化的胍基团、至少一个保护的胍基团、至少一个酰胺基团、至少一个质子化的酰胺基团、至少一个保护的酰胺基团、至少一个脲基团、至少一个质子化的脲基团、至少一个保护的脲基团、至少一个硫脲基团、至少一个质子化的硫脲基团，或至少一个保护的硫脲基团。生物活性分子与树枝状聚合物结合。一种增加药物生物利用度的方法包括将药物与本发明的树枝状聚合物结合。
• Dendrimers as Molecular Translocators
  申请人：Goodman Murray

  公开号：US20080221020A1

  公开（公告）日：2008-09-11

  Transport molecules include a dendrimer and a biologically active molecule. The dendrimer of such transport molecules includes at least one guanidine group, at least one protonated guanidine group, at least one protected guanidine group, at least one amidine group, at least one protonated amidine group, at least one protected amidine group, at least one ureido group, at least one protonated ureido group, at least one protected ureido group, at least one thioureido group, at least one protonated thioureido group, or at least one protected thioureido group. The biologically active molecule is bonded to the dendrimer. A method of increasing the bioavailability of a drug includes bonding the drug to a dendrimer of the invention.

  运输分子包括一个树状分子和一个生物活性分子。这种运输分子的树状分子包括至少一个鸟氨酸基团，至少一个质子化的鸟氨酸基团，至少一个保护的鸟氨酸基团，至少一个酰胺基团，至少一个质子化的酰胺基团，至少一个保护的酰胺基团，至少一个尿素基团，至少一个质子化的尿素基团，至少一个保护的尿素基团，至少一个硫脲基团，至少一个质子化的硫脲基团，或者至少一个保护的硫脲基团。生物活性分子与树状分子结合。一种增加药物生物利用度的方法包括将药物与本发明的树状分子结合。
• Novel small molecule guanidine Sigma1 inhibitors for advanced prostate cancer
  作者：Joseph M. Salvino、Yellamelli V.V. Srikanth、Rongliang Lou、Halley M. Oyer、Nan Chen、Felix J. Kim

  DOI：10.1016/j.bmcl.2017.03.030

  日期：2017.5

  Prostate cancer is the most frequently diagnosed malignancy and the leading cause of cancer related death in men. First line therapy for disseminated disease relies on androgen deprivation, leveraging the addiction of these tumors on androgens for both growth and survival. Treatment typically involves antagonizing the androgen receptor (AR) or blocking the synthesis of androgens. Recurrence is common and within 2-3 years patients develop castration resistant tumors that become unresponsive to AR-axis targeted therapies. In order to provide a more effective treatment, we are utilizing an approach that targets a key scaffolding protein, Sigma1 (also known as sigma-1 receptor), a unique 26-kilodalton integral membrane protein that is critical in stabilizing the AR. Herein we report on a new series of Sigmal compounds for lead optimization derived from a hybrid pharmacophore approach. (C) 2017 Elsevier Ltd. All rights reserved.
• Facile and Efficient Guanylation of Amines Using Thioureas and Mukaiyama's Reagent
  作者：Yaw Fui Yong、Jennifer A. Kowalski、Mark A. Lipton

  DOI：10.1021/jo962196k

  日期：1997.3.1
• Structure-activity study of oncocin: On-resin guanidinylation and incorporation of homoarginine, 4-hydroxyproline or 4,4-difluoroproline residues
  作者：Ashif Y. Shaikh、Fredrik Björkling、Dorota Zabicka、Magdalena Tomczak、Malgorzata Urbas、Ilona Domraceva、Agrita Kreicberga、Henrik Franzyk

  DOI：10.1016/j.bioorg.2023.106876

  日期：2023.12