N-tert-butyl-5-amino-4-(3-hydroxyphenyl)-2-(methylthio)thieno[2,3-d]pyrimidine-6-carboxamide | 301847-72-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: N-tert-butyl-5-amino-4-(3-hydroxyphenyl)-2-(methylthio)thieno[2,3-d]pyrimidine-6-carboxamide
• 英文别名: tert-butyl 5-amino-2-methylthio-4-(3-hydroxyphenyl)-thieno[2,3-d]pyrimidine-6-carboxamide；5-amino-N-tert-butyl-4-(3-hydroxyphenyl)-2-methylsulfanylthieno[2,3-d]pyrimidine-6-carboxamide
• CAS: 301847-72-3
• 化学式: C₁₈H₂₀N₄O₂S₂
• 分子量: 388.514
• InChiKey: KORCEMCZKYMFIO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  155
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-tert-butyl-5-amino-4-(3-hydroxyphenyl)-2-(methylthio)thieno[2,3-d]pyrimidine-6-carboxamide 、 N,N-二乙基氯甲酰胺 在 N,N-二异丙基乙胺 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 生成 tert-butyl 5-amino-2-methylthio-4-(3-(N,N-diethylamino)-carbonyloxy-phenyl)-thieno[2,3-d]pyrimidine-6-carboxamide
  参考文献：
  名称：

  Bicyclic heteroaromatic compounds

  摘要：

  根据通用式(I)，提供一个双环杂芳化合物，或其药学上可接受的盐，其中R1为(3-8C)环烷基，(2-7C)杂环烷基，(6-14C)芳基或(4-13C)杂芳基；均可选择地取代一个或多个取代基；R2为(1-4C)烷基，(2-4C)烯基，(2-4C)炔基，(6-14C)芳基或(4-13C)杂芳基；R3为(1-8C)烷基，(3-8C)环烷基，(2-7C)杂环烷基，(6-14C)芳基或(4-13C)杂芳基；Y为CH或N；Z为NH2或OH；A为S，N(H)，N(R)，O或一个键，B为N(H)，O或一个键；X1-X2为C═C，C(O)—NH，NH—C(O)，C(O)—O，O—C(O)，C═N，N═C或S或O。该发明的化合物可用于生育调节疗法。

  公开号：

  US20030225113A1
• 作为产物：
  描述：

  Org 41841 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 生成 N-tert-butyl-5-amino-4-(3-hydroxyphenyl)-2-(methylthio)thieno[2,3-d]pyrimidine-6-carboxamide
  参考文献：
  名称：

  Bicyclic heteroaromatic compounds

  摘要：

  根据通用式(I)，提供一个双环杂芳化合物，或其药学上可接受的盐，其中R1为(3-8C)环烷基，(2-7C)杂环烷基，(6-14C)芳基或(4-13C)杂芳基；均可选择地取代一个或多个取代基；R2为(1-4C)烷基，(2-4C)烯基，(2-4C)炔基，(6-14C)芳基或(4-13C)杂芳基；R3为(1-8C)烷基，(3-8C)环烷基，(2-7C)杂环烷基，(6-14C)芳基或(4-13C)杂芳基；Y为CH或N；Z为NH2或OH；A为S，N(H)，N(R)，O或一个键，B为N(H)，O或一个键；X1-X2为C═C，C(O)—NH，NH—C(O)，C(O)—O，O—C(O)，C═N，N═C或S或O。该发明的化合物可用于生育调节疗法。

  公开号：

  US20030225113A1

文献信息

• [EN] BICYCLIC HETEROAROMATIC COMPOUNDS<br/>[FR] COMPOSÉS HÉTÉROAROMATIQUE BICYCLIQUE
  申请人：AKZO NOBEL NV

  公开号：WO2002024703A1

  公开（公告）日：2002-03-28

  A bicyclic heteroaromatic compound according to general formula (I), or a pharmaceutically acceptable salt thereof, wherein R1 is (3-8C)cycloalkyl, (2-7C)heterocycloalkyl, (6-14C)aryl or (4-13C)heteroaryl; all optionally substituted with one or more substituents; R2 is (1-4C)alkyl, (2-4C)alkenyl, (2-4C)alkynyl, (6-14C)aryl or (4-13C)heteroaryl; R3 is (1-8C)alkyl, (3-8C)cycloalkyl, (2-7C)heterocycloalkyl, (6-14C)aryl or (4-13C)heteroaryl; Y is CH or N; Z is NH¿2? or OH; A is S, N(H), N(R), O or a bond and B is N(H), O or a bond; X1-X2 is C=C, C(O)-NH, NH-C(O), C(O)-O, O-C(O), C=N, N=C or S or O. The compounds of the invention can be used in fertility regulation therapies.

  根据一般式（I），或其药学上可接受的盐，其中R1是（3-8C）环烷基，（2-7C）杂环烷基，（6-14C）芳基或（4-13C）杂芳基；均可选用一个或多个取代基；R2是（1-4C）烷基，（2-4C）烯基，（2-4C）炔基，（6-14C）芳基或（4-13C）杂芳基；R3是（1-8C）烷基，（3-8C）环烷基，（2-7C）杂环烷基，（6-14C）芳基或（4-13C）杂芳基；Y是CH或N；Z是NH2或OH；A是S，N（H），N（R），O或键；B是N（H），O或键；X1-X2是C=C，C（O）-NH，NH-C（O），C（O）-O，O-C（O），C=N，N=C或S或O。本发明的化合物可用于生育调节治疗。
• Bicyclic heteroaromatic compounds useful as LH agonists
  申请人：——

  公开号：US20030212081A1

  公开（公告）日：2003-11-13

  The invention relates to a bicyclic heteroaromatic derivative compound according to general formula (II), 1 or a pharmaceutically acceptable salt thereof. The compounds of the invention have LH receptor activating activity and can be used in fertility regulating therapies.

  本发明涉及一种双环杂芳衍生物化合物，其通式为（II）1或其药学上可接受的盐。本发明的化合物具有LH受体激活活性，可用于生育调节疗法。
• Bicyclic heteroaromatic compound
  申请人：N.V. Organon

  公开号：EP1886999A2

  公开（公告）日：2008-02-13

  A bicyclic heteroaromatic compound according to general formula I, or a pharmaceutically acceptable salt thereof, wherein R1 is (6 -14C)aryl optionally substituted with one or more substituents; R2 is (1-4C)alkyl,; R3 is (1-8C)alkyl; Y is N; Z is NH2 or OH; A is S and B is N(H) or O; X1-X2 is C=C, S or O. The compounds of the invention can be used in fertility regulation therapies.

  符合通式 I 的双环杂芳香族化合物或其药学上可接受的盐、 其中 R1是任选被一个或多个取代基取代的(6-14C)芳基；R2是(1-4C)烷基；R3是(1-8C)烷基；Y是N；Z是NH2或OH；A是S，B是N(H)或O；X1-X2是C=C、S或O。 本发明的化合物可用于生育力调节疗法。
• Evaluation of Small-Molecule Modulators of the Luteinizing Hormone/Choriogonadotropin and Thyroid Stimulating Hormone Receptors:  Structure−Activity Relationships and Selective Binding Patterns
  作者：Susanna Moore、Holger Jaeschke、Gunnar Kleinau、Susanne Neumann、Stefano Costanzi、Jian-kang Jiang、John Childress、Bruce M. Raaka、Anny Colson、Ralf Paschke、Gerd Krause、Craig J. Thomas、Marvin C. Gershengorn

  DOI：10.1021/jm060247s

  日期：2006.6.1

  The substituted thieno[ 2,3-d] pyrimidine 3 ( Org 41841), a partial agonist for the luteinizing hormone/choriogonadotropin receptor ( LHCGR) and the closely related thyroid-stimulating hormone receptor ( TSHR), was fundamentally altered, and the resulting analogues were analyzed for their potencies, efficacies, and specificities at LHCGR and TSHR. Chemical modification of the parent compound combined with prior mutagenesis of TSHR provided compelling experimental evidence in support of computational models of 3 binding to TSHR and LHCGR within their transmembrane cores. Biochemical analysis of a specific modification to the chemical structure of 3 provides additional evidence of a H-bond between the ligand and a glutamate residue in transmembrane helix 3, which is conserved in both receptors. Several key interactions were surveyed to determine their respective biochemical roles in terms of both van der Waals dimensions and hydrogen bond capacity and the respective relationship to biological activity.
• BICYCLIC HETEROAROMATIC COMPOUNDS USEFUL AS LH AGONISTS
  申请人：Akzo Nobel N.V.

  公开号：EP1171443B1

  公开（公告）日：2005-07-13