N-(1,3-噻唑-2-基)氨基甲酰肼 | 3673-41-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: N-(1,3-噻唑-2-基)氨基甲酰肼
• 英文名称: 4-(2-thiazolyl)semicarbazide
• 英文别名: N-1,3-thiazol-2-ylhydrazinecarboxamide；4-(2-Thiazolyl)-semicarbazid；4-(Thiazol-2-yl)semicarbazide；1-amino-3-(1,3-thiazol-2-yl)urea
• CAS: 3673-41-4
• 化学式: C₄H₆N₄OS
• 分子量: 158.184
• InChiKey: VFJAIBUEXZUFGD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  108
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(1,3-噻唑-2-基)氨基甲酰肼 、 2′,3′,5′-tri-O-acetyl-2-nitrosoadenosine 在 溶剂黄146 作用下， 以 乙腈 为溶剂， 反应 4.0h， 以48%的产率得到2',3',5'-tri-O-acetyl-2-[3-(2-thiazolyl)aminocarbonyltriazene-1-yl]adenosine
  参考文献：
  名称：

  N⁶-Cyclopentyl-2-(3-phenylaminocarbonyltriazene-1-yl)adenosine (TCPA), a Very Selective Agonist with High Affinity for the Human Adenosine A₁ Receptor

  摘要：

  Four subtypes of adenosine receptors are currently known, that is, A(1), A(2A), A(2B), and A(3) receptors. Interestingly, quite substantial species differences exist especially between human and rat A(3) receptors. As a result, ligands such as CCPA, which are very selective for the rat A(1) and A(3) receptor versus the human A(3) receptor, are substantially less selective when the human A(1) and A(3) receptors are compared. New 2-substituted and 2,N-6-disubstituted adenosines were synthesized, and their affinities for the human adenosine A(1), A(2A), A(2B), and A(3) receptors were determined. Although large substituents on the C2-position are generally thought to yield adenosine A(2A) receptor selective ligands, the reported series of 2-triazeno-substituted adenosines had a very high affinity for the A(1) receptor. For example, 2-(3-phenylaminocarbonyltriazene-1-yl)adenosine had an affinity of 6.1 +/- 1.3 nM for the human adenosine A(1) receptor. Introduction of a diphenethyl substituent at the N-6-position of this compound resulted in a high-affinity agonist, 3.1 +/- 0.9 nM, for the human adenosine A(1) receptor with 316- and 45-fold selectivity versus the human A(2A) and human A(3) receptors, respectively. The most selective, high-affinity human adenosine A(1) receptor agonist was the disubstituted compound N-6-cyclopentyl-2-(3-phenylaminocarbonyltriazene-1-yl)adenosine (TCPA). TCPA had an affinity of 2.8 +/- 0.8 nM for the human adenosine A, receptor and was 75-fold and 214-fold selective versus the human A(2A) and human A(3) receptors, respectively. In addition, TCPA was a full agonist and inhibited the forskolin-induced cAMP production of CHO cells stably transfected with the human adenosine A(1) receptor with an IC50 of 1.5 +/- 0.5 nM.

  DOI：

  10.1021/jm021074j
• 作为产物：
  描述：

  苯基1,3-噻唑-2-基氨基甲酸酯 在 一水合肼 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以68%的产率得到N-(1,3-噻唑-2-基)氨基甲酰肼
  参考文献：
  名称：

  N⁶-Cyclopentyl-2-(3-phenylaminocarbonyltriazene-1-yl)adenosine (TCPA), a Very Selective Agonist with High Affinity for the Human Adenosine A₁ Receptor

  摘要：

  Four subtypes of adenosine receptors are currently known, that is, A(1), A(2A), A(2B), and A(3) receptors. Interestingly, quite substantial species differences exist especially between human and rat A(3) receptors. As a result, ligands such as CCPA, which are very selective for the rat A(1) and A(3) receptor versus the human A(3) receptor, are substantially less selective when the human A(1) and A(3) receptors are compared. New 2-substituted and 2,N-6-disubstituted adenosines were synthesized, and their affinities for the human adenosine A(1), A(2A), A(2B), and A(3) receptors were determined. Although large substituents on the C2-position are generally thought to yield adenosine A(2A) receptor selective ligands, the reported series of 2-triazeno-substituted adenosines had a very high affinity for the A(1) receptor. For example, 2-(3-phenylaminocarbonyltriazene-1-yl)adenosine had an affinity of 6.1 +/- 1.3 nM for the human adenosine A(1) receptor. Introduction of a diphenethyl substituent at the N-6-position of this compound resulted in a high-affinity agonist, 3.1 +/- 0.9 nM, for the human adenosine A(1) receptor with 316- and 45-fold selectivity versus the human A(2A) and human A(3) receptors, respectively. The most selective, high-affinity human adenosine A(1) receptor agonist was the disubstituted compound N-6-cyclopentyl-2-(3-phenylaminocarbonyltriazene-1-yl)adenosine (TCPA). TCPA had an affinity of 2.8 +/- 0.8 nM for the human adenosine A, receptor and was 75-fold and 214-fold selective versus the human A(2A) and human A(3) receptors, respectively. In addition, TCPA was a full agonist and inhibited the forskolin-induced cAMP production of CHO cells stably transfected with the human adenosine A(1) receptor with an IC50 of 1.5 +/- 0.5 nM.

  DOI：

  10.1021/jm021074j

文献信息

• [EN] INHIBITORS OF MALT1 PROTEASE<br/>[FR] INHIBITEURS DE LA PROTÉASE MALT1
  申请人：HELMHOLTZ ZENTRUM MÜNCHEN DEUTSCHES FORSCHUNGSZENTRUM FÜR GESUNDHEIT UND UMWELT GMBH

  公开号：WO2014086478A1

  公开（公告）日：2014-06-12

  The present invention relates to compounds which are inhibitors of mucosa-associated lymphoid tissue lymphoma translocation protein 1 (MALTl) and to their use in therapy, in particular in the treatment or prevention of a disease or disorder which is treatable by an inhibitor of a paracaspase. The present invention also relates to pharmaceutical compositions containing such compounds.

  本发明涉及作为粘膜相关淋巴组织淋巴瘤易位蛋白1（MALT1）抑制剂的化合物及其在治疗中的应用，尤其是在治疗或预防可通过抑制paracaspase治疗的疾病或失调中的应用。本发明还涉及含有该化合物的药物组合物。
• Avermectin derivatives
  申请人：Merck & Co., Inc.

  公开号：US04873224A1

  公开（公告）日：1989-10-10

  There are disclosed novel avermectin compounds wherein the 4" or 4' hydroxy group is oxidized to an oxo group and replaced with a semicarbazone, carbonyl- or sulfonyl- hydrazone, hydrazone, or oxime, and optionally reduced to the corresponding semicarbazide, carbonyl- or sulfonyl-hydrazide or hydrazine. The semicarbozones and hydrazones are prepared from the 4" or 4' oxo compound using the corresponding semicarbazides or hydrazines. The compounds have utility as anti-parasitic agents and compounds for that use are also disclosed. The compounds are also highly potent insecticides against agricultural pests. Compositions for such uses are also disclosed.

  揭示了新型阿维菌素化合物，其中4"或4'羟基被氧化成羟基酮，并替换为半卡巴肼、酰肼、磺酰肼、肼或肟，可选择还原为相应的半卡巴肼、酰肼、磺酰肼或肼。半卡巴肼和肼是从4"或4'酮化合物使用相应的半卡巴肼或肼制备的。这些化合物具有抗寄生虫剂的用途，并揭示了用于该用途的化合物。这些化合物也是高效的农业害虫杀虫剂。还揭示了用于此类用途的组合物。
• <i>N</i>⁶-Cyclopentyl-2-(3-phenylaminocarbonyltriazene-1-yl)adenosine (TCPA), a Very Selective Agonist with High Affinity for the Human Adenosine A₁ Receptor
  作者：Margot W. Beukers、Martin J. Wanner、Jacobien K. Von Frijtag Drabbe Künzel、Elisabeth C. Klaasse、Adriaan P. IJzerman、Gerrit-Jan Koomen

  DOI：10.1021/jm021074j

  日期：2003.4.1

  Four subtypes of adenosine receptors are currently known, that is, A(1), A(2A), A(2B), and A(3) receptors. Interestingly, quite substantial species differences exist especially between human and rat A(3) receptors. As a result, ligands such as CCPA, which are very selective for the rat A(1) and A(3) receptor versus the human A(3) receptor, are substantially less selective when the human A(1) and A(3) receptors are compared. New 2-substituted and 2,N-6-disubstituted adenosines were synthesized, and their affinities for the human adenosine A(1), A(2A), A(2B), and A(3) receptors were determined. Although large substituents on the C2-position are generally thought to yield adenosine A(2A) receptor selective ligands, the reported series of 2-triazeno-substituted adenosines had a very high affinity for the A(1) receptor. For example, 2-(3-phenylaminocarbonyltriazene-1-yl)adenosine had an affinity of 6.1 +/- 1.3 nM for the human adenosine A(1) receptor. Introduction of a diphenethyl substituent at the N-6-position of this compound resulted in a high-affinity agonist, 3.1 +/- 0.9 nM, for the human adenosine A(1) receptor with 316- and 45-fold selectivity versus the human A(2A) and human A(3) receptors, respectively. The most selective, high-affinity human adenosine A(1) receptor agonist was the disubstituted compound N-6-cyclopentyl-2-(3-phenylaminocarbonyltriazene-1-yl)adenosine (TCPA). TCPA had an affinity of 2.8 +/- 0.8 nM for the human adenosine A, receptor and was 75-fold and 214-fold selective versus the human A(2A) and human A(3) receptors, respectively. In addition, TCPA was a full agonist and inhibited the forskolin-induced cAMP production of CHO cells stably transfected with the human adenosine A(1) receptor with an IC50 of 1.5 +/- 0.5 nM.